乙基2-脱氧-2-(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)-3-O-(苯基甲基)-4,6-O-[(R)-苯基亚甲基]-1-硫代-BETA-D-吡喃葡萄糖苷 | 123212-53-3

分子结构分类

有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物

中文名称

乙基2-脱氧-2-(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)-3-O-(苯基甲基)-4,6-O-[(R)-苯基亚甲基]-1-硫代-BETA-D-吡喃葡萄糖苷

中文别名

——

英文名称

Ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

英文别名

Ethyl 3-O-benyl-4,6-O-[(R)-phenylmethylene]-1-thio-a-D-Mannopyranoside；2-[(2R,4aR,6S,7R,8R,8aS)-6-ethylsulfanyl-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]isoindole-1,3-dione

乙基2-脱氧-2-(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)-3-O-(苯基甲基)-4,6-O-[(R)-苯基亚甲基]-1-硫代-BETA-D-吡喃葡萄糖苷化学式

CAS

123212-53-3

化学式

C₃₀H₂₉NO₆S

mdl

——

分子量

531.629

InChiKey

LTAVTXCDXZSJBC-UHHZLRDHSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

683.0±55.0 °C(Predicted)
密度：

1.36±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

4.4
重原子数：

38
可旋转键数：

7
环数：

6.0
sp3杂化的碳原子比例：

0.33
拓扑面积：

99.6
氢给体数：

0
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
ETHYL4,6-O-BENZYLIDENE-2-DEOXY-2-PHTHALIMIDO-1-THIO-Β-D-GLUCOPYRANOSIDE乙基4,6-O-亚苄基-2-脱氧-2-邻苯二甲酰亚氨基-1-硫代-Β-D-吡喃葡萄糖苷	ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside	99409-33-3	C₂₃H₂₃NO₆S	441.505
乙基3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-1-硫代-β-D-吡喃葡萄糖苷	ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside	99409-32-2	C₂₂H₂₅NO₉S	479.508
2-脱氧-2-苯二酰亚胺-1,3,4,6-四-氧-乙酰-β-D-吡喃葡萄糖	1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose	10022-13-6	C₂₂H₂₃NO₁₁	477.425

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside	115533-35-2	C₃₀H₃₁NO₆S	533.645
——	ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside	854911-37-8	C₃₀H₃₁NO₆S	533.645
——	ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside	1421193-35-2	C₅₇H₅₇NO₁₁S	964.146
——	ethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopryanoside	177358-18-8	C₄₄H₄₉NO₁₅S	863.937
——	Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yl ester	860640-03-5	C₃₁H₃₀F₃NO₈S₂	665.708
——	2-((2S,3R,4R,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-oxo-tetrahydro-pyran-3-yl)-isoindole-1,3-dione	860640-09-1	C₃₀H₂₉NO₆S	531.629
——	3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-β-D-glucopyranosyl-1’,1’,1’-trichloroacetimidate	218961-09-2	C₃₀H₂₅Cl₃N₂O₇	631.897
——	O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide	344597-15-5	C₅₆H₄₉N₅O₁₂	984.031
甲基 3,6-二-O-苄基-2-脱氧-2-(1,3-二氧代-1,3-二氢-2H-异吲哚-2-基)吡喃己糖苷	methyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside	97242-79-0	C₂₉H₂₉NO₇	503.552
——	3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide	161315-66-8	C₂₈H₂₆N₄O₆	514.538
——	O-(-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide	214467-65-9	C₆₃H₅₇N₅O₁₂	1076.17
——	O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1*4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-β-D-glucopyranosyl azide	161315-68-0	C₅₆H₅₁N₅O₁₂	986.047
——	Ethyl 2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-1-thio-β-D-glucopyranoside	260392-74-3	C₂₈H₄₁N₃O₄SSi	543.803
——	Ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside	151992-76-6	C₂₂H₂₇N₃O₄S	429.54
——	Ethyl 2-amino-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside	260392-73-2	C₂₂H₂₉NO₄S	403.543
——	O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide	214467-61-5	C₅₁H₅₇N₅O₁₀	900.041
——	(2S,3R,4S,5R,6S)-3,5-Diazido-4-benzyloxy-2-benzyloxymethyl-6-ethylsulfanyl-tetrahydro-pyran	635309-99-8	C₂₂H₂₆N₆O₃S	454.553
——	(2S,3S,4S,5R,6S)-3,5-Diazido-4-benzyloxy-2-benzyloxymethyl-6-ethylsulfanyl-tetrahydro-pyran	635310-01-9	C₂₂H₂₆N₆O₃S	454.553
——	1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol	260392-75-4	C₆₃H₇₅N₃O₁₀Si	1062.39
——	1-Bromo-2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranoside	220679-83-4	C₂₆H₃₆BrN₃O₄Si	562.579

反应信息

作为反应物：

描述：

乙基2-脱氧-2-(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)-3-O-(苯基甲基)-4,6-O-[(R)-苯基亚甲基]-1-硫代-BETA-D-吡喃葡萄糖苷在盐酸、 sodium cyanoborohydride 作用下，以四氢呋喃、二氯甲烷、甲苯为溶剂，反应 22.83h，生成 phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-β-D-glucopyranosyl-(1-4)-3,6-di-O-benzyl-2-deoxy-2-N-phthalamido-β-D-glucopyranoside

参考文献：

名称：

‘Naked’ and Hydrated Conformers of the Conserved Core Pentasaccharide of N-linked Glycoproteins and Its Building Blocks

摘要：

N-glycosylation of eukaryotic proteins is widespread and vital to survival. The pentasaccharide unit -Man(3)GlcNAc(2)- lies at the protein-junction core of all oligosaccharides attached to asparagine side chains during this process. Although its absolute conservation impl