methyl 2,3,4-tri-O-benzyl-6-bromo-6-deoxy-α-D-galactopyranoside | 114871-48-6

分子结构分类

有机化合物 - 有机氧化合物

中文名称

——

中文别名

——

英文名称

methyl 2,3,4-tri-O-benzyl-6-bromo-6-deoxy-α-D-galactopyranoside

英文别名

(2S,3R,4S,5R,6S)-2-(bromomethyl)-6-methoxy-3,4,5-tris(phenylmethoxy)oxane

methyl 2,3,4-tri-O-benzyl-6-bromo-6-deoxy-α-D-galactopyranoside化学式

CAS

114871-48-6

化学式

C₂₈H₃₁BrO₅

mdl

——

分子量

527.455

InChiKey

GBRWKBAOTRGDCL-JYIVOWJTSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

598.0±50.0 °C(Predicted)
密度：

1.31±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

4.9
重原子数：

34
可旋转键数：

11
环数：

4.0
sp3杂化的碳原子比例：

0.36
拓扑面积：

46.2
氢给体数：

0
氢受体数：

5

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
——	methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside	55094-38-7	C₂₈H₃₂O₆	464.558
——	(2R,4aR,6S,7R,8S,8aS)-6-methoxy-2-phenyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine	7177-79-9	C₂₈H₃₀O₆	462.543
——	methyl 4,6-O-benzylidene-α-D-galactopyranoside	——	C₁₄H₁₈O₆	282.293
甲基2,3,4-三-O-(苯基甲基)-6-O-(三苯基甲基)-ALPHA-D-吡喃半乳糖苷	methyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-galactopyranoside	——	C₄₇H₄₆O₆	706.879
——	methyl 6-O-triphenylmethyl-α-D-galactopyranoside	——	C₂₆H₂₈O₆	436.505
Α-D-乳酸吡喃糖苷甲酯	methyl α-D-galactopyranoside	3396-99-4	C₇H₁₄O₆	194.185

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	methyl 2,3,4-tri-O-benzyl-α-D-fucopyranoside	156769-28-7	C₂₈H₃₂O₅	448.559
——	2,3,4-tri-O-benzyl-6-deoxy-α-D-galactopyranose	156719-47-0	C₂₇H₃₀O₅	434.532
——	allyl O-(2,3,4-tri-O-benzyl-6-deoxy-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzyl-6-deoxy-α-D-galactopyranoside	——	C₅₀H₅₆O₉	800.989
——	allyl O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-galactopyranosyl)-(1->4)-2,3-di-O-benzyl-6-deoxy-α-D-galactopyranoside	——	C₅₀H₅₆O₉	800.989

反应信息

作为反应物：

描述：

methyl 2,3,4-tri-O-benzyl-6-bromo-6-deoxy-α-D-galactopyranoside 在 palladium on activated charcoal 盐酸、 sodium tetrahydroborate 、氢气、氧气、 mercury(II) trifluoroacetate 、 sodium cyanoborohydride 、锌作用下，以乙醇为溶剂，反应 33.0h，生成 (2R,3S,4R,5S)-2-甲醇哌啶-3,4,5-三醇盐酸盐

参考文献：

名称：

（+）-1,5-dideoxy-1,5-imino-D-galactitol（一种有效的α-D-半乳糖苷酶抑制剂）的合成。

摘要：

DOI：

10.1016/0008-6215(87)80289-6
作为产物：

描述：

Α-D-乳酸吡喃糖苷甲酯在 lithium aluminium tetrahydride 、三氯化铝、 sodium hydride 、三乙胺、 lithium bromide 、 zinc(II) chloride 作用下，以乙醚、二氯甲烷、 N,N-二甲基甲酰胺、丁酮为溶剂，生成 methyl 2,3,4-tri-O-benzyl-6-bromo-6-deoxy-α-D-galactopyranoside

参考文献：

名称：

半乳糖和葡萄糖系列新的α-和β-宝石-二氟亚甲基C-糖苷的合成

摘要：

宝石-二氟亚甲基C-糖吡喃糖苷的合成可通过在醛上进行的Reformatsky反应以及随后的涉及环氧化物或氧汞化反应的分子内环化反应而得以有效实现。

DOI：

10.1016/s0040-4039(01)01144-3

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文献信息

In situ Activating Glycosylation of 6-Deoxysugars: Synthesis ofO-α-D-Fucosyl-(1→4)-O-α-D-fucosyl-(1→4)-O-α-D-quinovosyl-(1→4)-D-quinovose

作者：Shinkiti Koto、Ami Kusunoki、Motoko Hirooka

DOI：10.1246/bcsj.73.967

日期：2000.4

The linear tetrasaccharide, α-D-fucopyranosyl-(1→4)-α-D-fucopyranosyl-(1→4)-α-D-quinovopyranosyl-(1→4)-D-quinovopyranose, the sugar cluster of asterosaponin A from the starfish, Asterias amurensis, was synthesized in a convergent manner. We employed an in situ activating glycosylation using 1-OH sugar derivatives and a system of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine as well as a related system.

线性四糖α-D-岩藻吡喃糖基-(1→4)-α-D-岩藻吡喃糖基-(1→4)-α-D-奎诺吡喃糖基-(1→4)-D-奎诺吡喃糖，即海星（Asterias amurensis）中星皂苷A的糖簇，通过汇聚合成法被成功合成。我们采用了位点特异性活化的糖基化方法，使用1-羟基糖衍生物以及p-硝基苯磺酰氯、三氟甲磺酸银和三乙胺组成的一套糖基化系统及相关体系。
RCAI-61, the 6′-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo

作者：Takuya Tashiro、Ryusuke Nakagawa、Sayo Inoue、Masao Shiozaki、Hiroshi Watarai、Masaru Taniguchi、Kenji Mori

DOI：10.1016/j.tetlet.2008.09.074

日期：2008.11

RCAI-61, the 6'-O-methylated analog of KRN7000, and six other analogs with modified 6'-position of the galactose moiety of KRN7000 were synthesized to examine their bioactivity for mouse lymphocytes. Methyl alpha-D-galactopyranoside was the starting material for RCAI-58, 61, 64, 83, 85, and 86, while RCAI-87 was prepared from methyl beta-L-arabinopyranoside. Bioassay showed RCAI-61 to be a Much more potent stimulant of mouse lymphocytes than KRN7000 and RCAI-56 to induce the production of a large amount of IFN-gamma in vivo. (C) 2008 Elsevier Ltd. All rights reserved.
Study of Uridine 5′-Diphosphate (UDP)-Galactopyranose Mutase Using UDP-5-Fluorogalactopyranose as a Probe: Incubation Results and Mechanistic Implications

作者：Geng-Min Lin、He G. Sun、Hung-wen Liu

DOI：10.1021/acs.orglett.6b01618

日期：2016.7.15

Uridine 5'-diphosphate-5-fluorogalactopyranose (UDP-SF-Galp, 7) was synthesized, and its effect on UDP-Galp mutase (UGM) was investigated. UGM facilitated the hydrolysis of 7 to yield UDP and 5-oxogalactose (24), but no 11 was detected. F-19 NMR and trapping experiments demonstrated that the reaction involves the initial formation of a substrate-cofactor adduct followed by decomposition of the resulting C5 gem-fluorohydrin to generate a 5-oxo intermediate (10). The results support the current mechanistic proposal for UGM and suggest new directions for designing mechanism-based inhibitors.
Bartnicka; Zamojski, Polish Journal of Chemistry, 1998, vol. 72, # 4, p. 688 - 693

作者：Bartnicka、Zamojski

DOI：——

日期：——
Synthesis of (+)-1,5-dideoxy-1,5-imino-d-galactitol, a potent α-d-galactosidase inhibitor

作者：Ronald C. Bernotas、Michael A. Pezzone、Bruce Ganem

DOI：10.1016/0008-6215(87)80289-6

日期：1987.9