2,3,4-tri-O-trimethylsilyl-6-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranosyl-(1→1)-2,3,4-tri-O-trimethylsilyl-6'-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranoside | 1170667-13-6

分子结构分类

有机化合物 - 脂质和类脂质分子 - 糖脂

中文名称

——

中文别名

——

英文名称

2,3,4-tri-O-trimethylsilyl-6-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranosyl-(1→1)-2,3,4-tri-O-trimethylsilyl-6'-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranoside

英文别名

——

2,3,4-tri-O-trimethylsilyl-6-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranosyl-(1→1)-2,3,4-tri-O-trimethylsilyl-6'-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranoside化学式

CAS

1170667-13-6

化学式

C₂₁₂H₄₃₀O₁₇Si₈

mdl

——

分子量

3476.42

InChiKey

FUHPETVPYPDSNI-YJDKSYPRSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

72.48
重原子数：

237.0
可旋转键数：

180.0
环数：

4.0
sp3杂化的碳原子比例：

0.99
拓扑面积：

172.59
氢给体数：

0.0
氢受体数：

17.0

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	2,3,4,2',3',4'-hexakis-O-(trimethylsilyl)-α,α-trehalose	59578-12-0	C₃₀H₇₀O₁₁Si₆	775.392

反应信息

作为反应物：

描述：

2,3,4-tri-O-trimethylsilyl-6-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranosyl-(1→1)-2,3,4-tri-O-trimethylsilyl-6'-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranoside 在四丁基氟化铵作用下，以四氢呋喃为溶剂，反应 1.0h，以78%的产率得到6-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranosyl-(1→1)-6'-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranoside

参考文献：

名称：

The first unique synthetic mycobacterial cord factors

摘要：

Synthetic mycolic acids matching the overall structure of the major alpha- and methoxy-mycolic acids of Mycobacterium tuberculosis are coupled to trehalose to generate the corresponding synthetic trehalose dimycolate (TDM; cord factor) and trehalose monomycolate (TMM). (C) 2009 Elsevier Ltd. All rights reserved.

DOI：

10.1016/j.tetlet.2009.03.213
作为产物：

描述：

2,3,4,2',3',4'-hexakis-O-(trimethylsilyl)-α,α-trehalose 、 (R)-2-{(R)-1-(tert-butyldimethylsilanyloxy)-18-[(1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl]octadecyl}hexacosanoic acid 在 4-二甲氨基吡啶、盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺作用下，以二氯甲烷为溶剂，反应 144.0h，以51%的产率得到2,3,4-tri-O-trimethylsilyl-6-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranosyl-(1→1)-2,3,4-tri-O-trimethylsilyl-6'-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranoside

参考文献：

名称：

The first unique synthetic mycobacterial cord factors

摘要：

Synthetic mycolic acids matching the overall structure of the major alpha- and methoxy-mycolic acids of Mycobacterium tuberculosis are coupled to trehalose to generate the corresponding synthetic trehalose dimycolate (TDM; cord factor) and trehalose monomycolate (TMM). (C) 2009 Elsevier Ltd. All rights reserved.

DOI：

10.1016/j.tetlet.2009.03.213

点击查看最新优质反应信息

文献信息

Synthetic trehalose di- and mono-esters of α-, methoxy- and keto-mycolic acids

作者：Juma'a R. Al Dulayymi、Mark S. Baird、Maximiliano Maza-Iglesias、Rwoa'a T. Hameed、Klarah S. Baols、Majed Muzael、Ahmed D. Saleh

DOI：10.1016/j.tet.2014.10.072

日期：2014.12

Synthetic mycolic acids matching the overall structure of the major mycolic acids of Mycobacterium tuberculosis are coupled to trehalose to generate the corresponding synthetic trehalose monomycolate (TMM) and trehalose dimycolate (TDM; cord factor), either with two identical or two different mycolic acids. (C) 2014 Elsevier Ltd. All rights reserved.

同类化合物

霉酚酸苯酚beta-D-葡糖苷阜孢霉素B 阜孢杀菌素蔗糖棕榈酸酯蔗糖四异硬脂酸酯蔗糖七月桂酸酯药喇叭(IPOMOEAPURGA)树脂纤维素二糖八壬烷酸酯硫脂I 石斛碱;青藤碱甲基6-O-(2-十四烷基-3-羟基十八碳酰基)-alpha-D-吡喃葡萄糖苷环戊羧酸,1-氨基-2-甲基-,(1R,2S)-rel- 特女贞苷海藻糖6,6'-二甲藻酸酯海藻糖 6,6'-二山嵛酸酯水螅毒素木松香II 木松香I 单岩藻糖基乳糖-N-四糖二唾液酸乳-N-四糖乳糖醛酸乙醋化己二酸双淀粉中文名称暂缺 β-D-呋喃果糖基-α-D-吡喃葡萄苷二硬脂酸酯 Β-D-呋喃果糖基-Α-D-吡喃葡糖苷十二酸双酯 alpha-D-吡喃葡萄糖苷, 6-O-(1-氧代癸基)-alpha-D-吡喃葡萄糖基, 6-癸酸酯 alpha-D-吡喃葡萄糖基-alpha-D-吡喃葡萄糖苷 6-(3-羟基-2-十四烷基十八烷酸酯) [(3aR,5R,5aR,8aS,8bR)-2,2,7,7-四甲基四氢-3aH-二[1,3]二噁唑并[4,5-b:4',5'-d]吡喃-5-基]甲基丁酸酯(non-preferredname) [(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6R)-6-(十六烷酰氧基甲基)-3,4,5-三羟基四氢吡喃-2-基]氧基-3,4,5-三羟基四氢吡喃-2-基]甲基十六烷酸酯 [(2R,3S,4S,5R)-3,4-二羟基-2,5-二(羟基甲基)四氢呋喃-2-基][(2R,3S,4S,5R,6S)-3,4,5,6-四羟基四氢吡喃-2-基]甲基2-甲基-4-(2-甲基癸-1-烯-4-基)己二酸酯 [(2R,3R,4S,5R,6R)-6-[[(1R,2R,3R,4R,6R)-2,3-二羟基-5,8-二氧杂双环[4.2.0]辛烷-4-基]氧基]-3,4,5-三羟基四氢吡喃-2-基]甲基3-羟基-2-十四烷基十八烷酸酯 N-乙酰基-硫代胞壁酰-丙氨酰-异谷氨酰胺 N-(O-alpha-D-甘露糖基-(1-3)-O-(O-alpha-D-甘露糖基-(1->3)-O-(alpha-D-甘露糖基-(1-6))-alpha-D-甘露糖基-(1-6))-O-beta-D-甘露糖基-(1->4)-O-2-(乙酰氨基)-2-脱氧-beta-D-吡喃葡萄糖基-(1->4)-2-(乙酰氨基)-2-脱氧-beta-D-吡喃葡萄糖基)-L-天冬氨酰胺 L-缬氨酰-L-丙氨酰-L-缬氨酰甘氨酰-L-α-谷氨酰-L-α-谷氨酰-L-脯氨酰甘氨酰-L-脯氨酰-N~5~-(二氨基甲亚基)-L-鸟氨酸酰胺 D-甘露糖基-(1-6)-D-甘露糖基-(1-4)-2-乙酰氨基-2-脱氧-D-吡喃葡萄糖基-(1-4)-2-乙酰氨基-1-N-(4'-L-天冬氨酰)-2-脱氧-beta-D-吡喃葡萄糖基胺 D-吡喃葡糖酐-2,6-双油酸酯与聚环氧乙烷(2:1)的醚化物 D-(+)-海藻糖6-单油酸酯 9,10-二氯-2,6-二甲基蒽 8-甲氧基羰基辛基2-O-（aL-呋喃基呋喃糖基）-3-O-（aD-吡喃半乳糖基）-bD-吡喃半乳糖苷 6-山慈菇甙A 6-O-alpha-D-吡喃半乳糖基-D-葡萄糖酸 6,6'-二((2R,3R)-3-羟基-2-十四烷基十八烷酸酯)-海藻糖 4H-吡咯并[3,2,1-脱]蝶啶,5,6-二氢-4,5-二甲基-(9CI) 4-嘧啶甲腈,2-苯基- 4-[[(2R)-2-羟基-3,3-二甲基-4-[(2R,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基丁酰基]氨基]丁酸 4-[6-(1,2-二羟基乙基)-3,4,5-三羟基-四氢吡喃-2-基]氧基-2,3,5-三羟基-7,8-二氧代-辛酸 3-O-棕榈酰-beta-D-呋喃果糖基2,3-二-O-棕榈酰-alpha-D-吡喃葡萄糖苷 3-(6H-苯并[b][1,5]苯并噁噻庚英-6-基)丙基-二甲基-铵2-羟基-2-羰基-乙酸酯 2-脱氧-3-O-[(3R)-3-羟基十四烷酰基]-2-{[(3R)-3-羟基十四烷酰基]氨基}-1-O-膦酰-alpha-D-吡喃葡萄糖 2-氨基-6-[[3,5,6-三羟基-2-氧代-4-[3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基己基]氨基]己酸