benzyl oleanolate 3-O-3,4-O-isopropylidene-α-L-arabinopyranoside | 875878-34-5

分子结构分类

有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质

中文名称

——

中文别名

——

英文名称

benzyl oleanolate 3-O-3,4-O-isopropylidene-α-L-arabinopyranoside

英文别名

benzyl oleanolate 3-O-3′,4′-O-isopropylidene-α-L-arabinopyranoside；benzyl 3-O-(3,4-O-isopropylidene-α-L-arabinopyranosyl)-oleanolate；benzyl (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[[(3aS,6S,7R,7aR)-7-hydroxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate

benzyl oleanolate 3-O-3,4-O-isopropylidene-α-L-arabinopyranoside化学式

CAS

875878-34-5

化学式

C₄₅H₆₆O₇

mdl

——

分子量

719.015

InChiKey

UYYUJFDYZHBUMW-RORPIGTKSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

736.9±60.0 °C(Predicted)
密度：

1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

辛醇/水分配系数(LogP)：

9.3
重原子数：

52
可旋转键数：

6
环数：

8.0
sp3杂化的碳原子比例：

0.8
拓扑面积：

83.4
氢给体数：

1
氢受体数：

7

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
——	benzyl oleanolate 3-O-α-L-arabinopyranoside	875878-33-4	C₄₂H₆₂O₇	678.95
——	benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-arabinopyranoside	875878-32-3	C₆₃H₇₄O₁₀	991.275
齐墩果酸苄酯	oleanolic acid benzyl ester	303114-51-4	C₃₇H₅₄O₃	546.834

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	benzyl oleanolate 3-O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-L-arabinopyranoside	1355346-19-8	C₅₇H₈₂O₁₄	991.27
——	benzyl oleanolate 2,4-di-O-acetyl-3-O-levulinoyl-α-L-rhamnopyranosyl-(1 → 2)-3,4-O-isopropylidene-α-L-arabinopyranoside	1445703-79-6	C₆₀H₈₆O₁₅	1047.33
——	benzyl oleanolate 3-O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside	1637228-51-3	C₅₄H₇₈O₁₄	951.205
——	benzyl oleanolate 3-O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)-4-O-acetyl-α-L-arabinopyranoside	1637228-49-9	C₅₆H₈₀O₁₅	993.242
——	benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-O-isopropylidene-α-L-arabinopyranoside	875878-35-6	C₇₂H₈₈O₁₄	1177.48
——	benzyl oleanolate 3-O-2″,3″,4″,6″-tetra-O-benzoyl-β-D-glucopyranosyl-(1→2)-3′,4′-O-isopropylidene-α-L-arabinopyranoside	1229037-82-4	C₇₉H₉₂O₁₆	1297.59
——	benzyl oleanolate 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1 → 3)-2,4-di-O-acetyl-α-L-rhamnopyranosyl-(1 → 2)-3,4-O-isopropylidene-α-L-arabinopyranoside	1352410-45-7	C₈₁H₁₀₀O₂₀	1393.67
——	benzyl 3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranosyl-(1->2)-3,4-O-isopropylidene-α-L-arabinopyranosyl]oleanolate	1268673-31-9	C₈₉H₁₀₆O₂₂	1527.81
——	benzyl oleanolate 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1 → 4)-2,3-di-O-benzoyl-β-D-xylopyranosyl-(1 → 3)-2,4-di-O-acetyl-α-L-rhamnopyranosyl-(1 → 2)-3,4-O-isopropylidene-α-L-arabinopyranoside	1352410-44-6	C₁₀₈H₁₂₂O₂₈	1868.14
——	benzyl 3-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl)-oleanolate	875878-36-7	C₆₉H₈₄O₁₄	1137.42
——	benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3-O-benzoyl-α-L-arabinopyranoside	875878-30-1	C₇₆H₈₈O₁₅	1241.53
——	benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-4-O-acetyl-α-L-arabinopyranoside	875878-29-8	C₇₁H₈₆O₁₅	1179.45
beta-常春藤素	β-hederin	35790-95-5	C₄₁H₆₆O₁₁	734.968

反应信息

作为反应物：

描述：

benzyl oleanolate 3-O-3,4-O-isopropylidene-α-L-arabinopyranoside 在 palladium on activated charcoal 4 A molecular sieve 、三氟化硼乙醚、氢气、对甲苯磺酸作用下，以甲醇、二氯甲烷、乙酸乙酯为溶剂，反应 5.0h，生成

参考文献：

名称：

Synthesis of β-hederin and Hederacolchiside A1: triterpenoid saponins bearing a unique cytotoxicity-inducing disaccharide moiety

摘要：

A facile synthetic approach toward oleanolic acid glycoside bearing alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl moiety, a unique oligosaccharide that strongly induces antitumor activity of oleanane-type triterpenoid saponins, was developed. Based on this approach P-hederin (oleanolic acid 3-0-Gt-L-rhamnopyranosyl-(1 -> 2)-alpha- L-arabinopyrano side) was efficiently prepared from oleanolic acid through stepwise glycosylation in linear eight steps with 52% overall yield, while Hederacolchiside A, (oleanolic acid 3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-[beta-D-glucopyranosyl-(1 -> 4)]-alpha-L-arabinopyranoside) in linear 13 steps with 20% overall yield. (c) 2005 Published by Elsevier Ltd.

DOI：

10.1016/j.carres.2005.10.015
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