CAS: 14086-90-9; (3R,4R,5S,6R)-3-Acetamido-6-(Acetoxymethyl)Tetrahydro-2H-Pyran-2,4,5-Triyl Triacetate

该化合物是碳水化合物化学的关键中间体,广泛用于合成甘蓝氨基甘油和其他生物活性甘油化合物,其完全的乙基结构增强了有机溶剂的稳定性和溶性,促进了高效的相合反应.在厌食中心的α配置对于立体选择性甘油债券形成特别有利.该化合物是N-乙基甘基氨衍生物的多用途前体,在基因生物学研究和药物应用中至关重要.其高纯度和定义明确的立体化学使其成为合成和机械学研究的可靠选择.保护性乙基酸组可以在温和的条件下有选择地去除,从而能够进一步实现功能化.

英文名称(3R,4R,5S,6R)-3-Acetamido-6-(Acetoxymethyl)Tetrahydro-2H-Pyran-2,4,5-Triyl Triacetate
中文名称2-乙酰氨基-1,3,4,6-O-四乙酰基-2-脱氧-α-D-吡喃葡萄糖
IUPAC名称(3R,4R,5S,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate
其它别名D-Glucosamine Pentaacetate; 2-Acetamido-2-Deoxy-1,3,4,6-Tetra-0-Acetyl-Alpha-D-Glucopyranose; 2-Acetamido-1,3,4,6-Tetra-O-Acetyl-2-Deoxy-Alpha-D-Glucopyranose; 1,3,4,6-Tetra-O-Acetyl-2-(Acetylamino)-2-Deoxy-D-Glucopyranose, D-Glucosamine Pentaacetate, 1,3,4,6-Tetra-O-Acetyl-Glcnac, Glcnac Tetraacetate; 2-Acetamido-1,3,4,6-Tetra-O-Acetyl-2-Deoxy-D-Glucopyranose Min. ; β-D-Glcnac Tetraacetate; Beta-D-Glcnac Tetraacetate; (3R,4R,5S,6R)-3-Acetamido-6-(Acetoxymethyl)Tetrahydro-2H-Pyran-2,4,5-Triyl Triacetate
CAS编号14086-90-9
MFCD编号:MFCD00067367
EINECS号:231-865-4
分子式:C16H23NO10分子量:389.36
产品CID: 627806
产品分类生物化工 → 糖类化合物 → 单糖

相似结构搜索
InChIKey: OVPIZHVSWNOZMN-XIHUBIEQSA-N
InChI=1S/C16H23NO10/c1-7(18)17-13-15(25-10(4)21)14(24-9(3)20)12(6-23-8(2)19)27-16(13)26-11(5)22/h12-16H,6H2,1-5H3,(H,17,18)/t12-,13-,14-,15-,16?/m1/s1
计算化学: 氢键受体数10.0氢键供体数1.0可旋转键数10.0

MSDS等安全信息

警示词Warning
危险描述H302-H315-H319-H335-
防范说明P261-P305+P351+P338-

上下游产品

acetic anhydride 2-amino-2-deoxy-D-idose; hydr°Chloride 1,3,4,6-tetra-O-acetyl-D-glucosamine hydr°Chloride D-(+)-glucosamine hydr°Chloride p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline methyl 2-acetamido-3,4,6-O-triacetyl-2-deoxy-β-D-glucopyranoside

合成工艺路线路线简述

📜Benzyl 3-O-Allyl-2-Benzamido-4,6-O-Benzylidene-2-Deoxy-β-D-Glucopyranoside置于palladium On Activated Charcoal 吡啶,Lithium Aluminium Tetrahydride,氢气,4-甲基苯磺酸吡啶,Sodium Hydride,Mercury Dichloride,Mercury(II) Oxide体系中,用吡啶,乙醚,水,溶剂黄146,N,N-二甲基甲酰胺用作溶剂,化学反应 48.0H,反应生成2-乙酰氨基-1,3,4,6-O-四乙酰基-2-脱氧-Alpha-D-吡喃葡萄糖
参考文献:N-Allyl And N-Benzyl Derivatives Of 2-Amino-2-Deoxy-D-Glucose
标题:N-Allyl And N-Benzyl Derivatives Of 2-Amino-2-Deoxy-D-Glucose
摘要:
Doi:10.1016/s0008-6215(00)81058-7

海关参考信息

2905122000-异丙醇
2905310000-1,2-乙二醇
2905320000-1,2-丙二醇
2905399001-1,3-丙二醇
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:WO-9616071-A1
优先权日:1994-11-21
标题:PROCESSES FOR THE SYNTHESIS OF 3'-SUBSTITUTED LEWISx COMPOUNDS
发明人：SRIVASTAVA OM; IPPOLITO ROBERT; SRIVASTAVA GEETA; SZWEDA ROMAN; OHUCHI TOSHIO
权利人:GLYCOMED INC; SRIVASTAVA OM; IPPOLITO ROBERT; SRIVASTAVA GEETA; SZWEDA ROMAN; OHUCHI TOSHIO
摘要:Disclosed are processes for the chemical synthesis of 3'-substituted Lewis-OR compounds where R is an aglycon of at least one carbon atom. One particular compound prepared by the processes of this invention is 8-methoxycarbonyl-octyl-2-acetamido-3-O-( alpha -L-fucopyranosyl)-4-O-[3-O-sulfo- beta -D-galactopyranosyl]-2-deoxy- beta -D-glucopyranoside.

专利号:WO-9734623-A1
优先权日:1996-03-21
标题:Solid phase lipoglycopeptide library, compositions and methods
发明人：SOFIA MICHAEL; ALLANSON NIGEL; CHEN ANNA; LIU DASHAN; CHAN TIN YAU
权利人:TRANSCELL TECHNOLOGIES INC
摘要:The present invention relates to a library of distinct substances and compositions having the general formula R-P-S-L and P-S-L, representing solid support-bound lipoglycopeptides and free lipoglycopeptides, respectively. Combinatorial methods for the preparation of various libraries are described, as well as an assay for determining the biological activity of selected members thereof. In a specific embodiment, inhibitors of bacterial peptidoglycan synthesis are described.

其他信息查阅

供应商参考报价(招募中)

品牌试剂参考报价(招募中)

实用工具

📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

主要参考文献

参考标题:Synthesis Of A Difunctional Orthogonal Coupler For The Preparation Of Carbohydrate-Functionalized Sp(Eo-Stat-Po) Hydrogels
作者:Thorsten Anders,Kathrin Adamiak,Helmut Keul,Lothar Elling,Martin Möller |发布日期:2011.9.9
摘要:The Synthesis And Characterization Of A New Difunctional Coupler (4) Based On Trimethylolpropane (Tmp) Are Described. The Coupler Is Used To Connect Biologically Active N‐acetylglucosamine (Glcnac) On Amino‐reactive Microtiter Plates And On Star‐shaped Poly[(Ethylene Oxide)‐stat‐(Propylene Oxide)] Hydrogel Layers In Microtiter Plates. The Biological Activity Of Immobilized Carbohydrates Is Determined

合成参考文献

参考文献:10.1007/s10719-005-5060-1
摘要:Berkin A, Szarek WA, Kisilevsky R. Biological evaluation of a series of 2-acetamido-2-deoxy-D-glucose analogs towards cellular glycosaminoglycan and protein synthesis in vitro. Glycoconj J. 2005 Nov;22(7-9):443–51. doi: 10.1007/s10719-005-5060-1.