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2-(trimethylsilyl)ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside | 81336-82-5

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

2-(trimethylsilyl)ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

英文别名

(2R,3S,4R,5R,6R)-5-Acetamido-2-(acetoxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4-diyl Diacetate；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-(2-trimethylsilylethoxy)oxan-2-yl]methyl acetate

2-(trimethylsilyl)ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside化学式

CAS

81336-82-5

化学式

C₁₉H₃₃NO₉Si

mdl

——

分子量

447.558

InChiKey

UEDMXWQZSLUWPS-FVVUREQNSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

542.1±50.0 °C(Predicted)
密度：

1.15±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

1.0
重原子数：

30
可旋转键数：

12
环数：

1.0
sp3杂化的碳原子比例：

0.79
拓扑面积：

127
氢给体数：

1
氢受体数：

9

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-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose	70749-28-9	C₁₄H₂₁NO₉	347.322
β-D-葡萄糖胺五乙酸酯	2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose	7772-79-4	C₁₆H₂₃NO₁₀	389.359
——	2-(trimethylsilyl)ethyl 2-acetamido-2-deoxy-β-D-glucopyranoside	110891-63-9	C₁₃H₂₇NO₆Si	321.446
2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯	Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester	3068-34-6	C₁₄H₂₀ClNO₈	365.768
(3aR)-2-甲基-5alpha-(乙酰氧基甲基)-6beta,7alpha-二乙酰氧基-3Aalpha,6,7,7Aalpha-四氢-5H-吡喃并[3,2-d]恶唑	2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline	35954-65-5	C₁₄H₁₉NO₈	329.307

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose	70749-28-9	C₁₄H₂₁NO₉	347.322
β-D-葡萄糖胺五乙酸酯	2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose	7772-79-4	C₁₆H₂₃NO₁₀	389.359
A-D-氨基葡萄糖五乙酸盐	Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester	7784-54-5	C₁₆H₂₃NO₁₀	389.359
2-乙酰氨基-1,3,4,6-O-四乙酰基-2-脱氧-alpha-D-吡喃葡萄糖	2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate	14086-90-9	C₁₆H₂₃NO₁₀	389.359
——	2-(trimethylsilyl)ethyl 2-deoxy-4,6-O-isopropylidene-3-O-tetradecanoyl-2-<(3R)-3-tetradecanoyloxytetradecanamido>-β-D-glucopyranoside	122078-74-4	C₅₆H₁₀₇NO₉Si	966.552
——	2-(trimethylsilyl)ethyl 2-deoxy-3-O-tetradecanoyl-2-<(3R)-3-tetradecanoyloxytetradecanamido>-β-D-glucopyranoside	122099-30-3	C₅₃H₁₀₃NO₉Si	926.488
——	N-[(4aR,6R,7R,8R,8aS)-8-Hydroxy-2,2-dimethyl-6-(2-trimethylsilanyl-ethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide	125034-30-2	C₁₆H₃₁NO₆Si	361.511
——	2-(trimethylsilyl)ethyl 2-acetamido-2-deoxy-β-D-glucopyranoside	110891-63-9	C₁₃H₂₇NO₆Si	321.446
——	2-(trimethylsilyl)ethyl 2-acetamido-2-deoxy-β-D-galactopyranoside	125034-29-9	C₁₃H₂₇NO₆Si	321.446
——	2-(trimethylsilyl)ethyl 2-deoxy-4,6-O-isopropylidene-2-<(3R)-3-<2-(trimethylsilyl)ethoxymethoxy>tetradecanamido>-β-D-glucopyranoside	122078-75-5	C₃₄H₆₉NO₈Si₂	676.095
——	2-(trimethylsilyl)ethyl 2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside	122078-73-3	C₂₈H₅₅NO₇Si	545.833
——	2-(trimethylsilyl)ethyl 6-O-tert-butyldimethylsilyl-2-deoxy-3-O-tetradecanoyl-2-<(3R)-3-tetradecanoyloxytetradecanamido>-β-D-glucopyranoside	122528-74-9	C₅₉H₁₁₇NO₉Si₂	1040.75
——	2-(trimethylsilyl)ethyl 4-O--6-O-(3-carboxypropanoyl)-2-deoxy-3-O-tetradecanoyl-2-<(3R)-3-tetradecanoyloxytetradecanamido>-β-D-glucopyranoside	121885-19-6	C₆₁H₁₁₀Cl₆NO₁₅PSi	1369.32
——	2-(trimethylsilyl)ethyl 4-O--2-deoxy-3-O-tetradecanoyl-2-<(3R)-3-tetradecanoyloxytetradecanamido>-β-D-glucopyranoside	122501-67-1	C₅₇H₁₀₆Cl₆NO₁₂PSi	1269.25
——	2-(trimethylsilyl)ethyl 4-O--6-O-tert-butyldimethylsilyl-2-deoxy-3-O-tetradecanoyl-2-<(3R)-3-tetradecanoyloxytetradecanamido>-β-D-glucopyranoside	122501-66-0	C₆₃H₁₂₀Cl₆NO₁₂PSi₂	1383.51
——	2-(trimethylsilyl)ethyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside	122078-72-2	C₁₄H₂₉NO₅Si	319.473
5H-吡喃并[3,2-d]噁唑-5-甲醇,6,7-二(乙酰氧基)-3a,6,7,7a-四氢-2-甲基-,乙酸酯(ester)	acetic acid (3aR,5R,6R,7R,7aR)-6-acetoxy-5-acetoxymethyl-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-7-yl ester	10378-06-0	C₁₄H₁₉NO₈	329.307
(3aR)-2-甲基-5alpha-(乙酰氧基甲基)-6beta,7alpha-二乙酰氧基-3Aalpha,6,7,7Aalpha-四氢-5H-吡喃并[3,2-d]恶唑	2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline	35954-65-5	C₁₄H₁₉NO₈	329.307

反应信息

作为反应物：

描述：

2-(trimethylsilyl)ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 sodium methylate 作用下，以甲醇为溶剂，反应 0.5h，生成 2-(trimethylsilyl)ethyl 2-acetamido-2-deoxy-β-D-glucopyranoside

参考文献：

名称：

Ogawa, Yuji; Kitagawa, Masayuki; Fujishima, Yushun, Agricultural and Biological Chemistry, 1989, vol. 53, # 4, p. 1025 - 1036

摘要：

DOI：
作为产物：

描述：

2-(三甲硅基)乙醇、 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose 在硫酸、三氯化铁作用下，生成 2-(trimethylsilyl)ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

参考文献：

名称：

Ogawa, Yuji; Kitagawa, Masayuki; Fujishima, Yushun, Agricultural and Biological Chemistry, 1989, vol. 53, # 4, p. 1025 - 1036

摘要：

DOI：

点击查看最新优质反应信息

文献信息

Chemistry of β-trimethylsilylethanol. II. A new method for protection of an anomeric center in pyranosides

作者：Bruce H. Lipshutz、Joseph J. Pegram、Matthew C. Morey

DOI：10.1016/s0040-4039(01)82992-0

日期：1981.1

Protection of the anomeric center in various carbohydrates as a β-trimethylsilylethyl glycoside is reported. The free sugar can be regenerated using LiBF4 in acetonitrile.

据报道，作为β-三甲基甲硅烷基乙基糖苷，各种碳水化合物中的异头异构中心得到保护。可以使用乙腈中的LiBF 4再生游离糖。
New procedure for the preparation of 2-(trimethylsilyl)ethyl and other alkyl β-glycosides

作者：C. Gregory Sowell、Mark T. Livesay、David A. Johnson

DOI：10.1016/0040-4039(95)02233-3

日期：1996.1

The title compound and other alkyl β-glycosides 1a-g can be prepared in one step from commercially available (3) and simple alcohols using camphorsulfonic acid as a promoter together with azeotropic removal of acetic acid.

标题化合物和其他烷基β-糖苷1a-g可使用樟脑磺酸作为促进剂并通过共沸除去乙酸，由市售（3）和简单的醇一步制备。
2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars

作者：Karl Jansson、Stefan Ahlfors、Torbjoern Frejd、Jan Kihlberg、Goeran Magnusson、Jan Dahmen、Ghazi Noori、Kristina Stenvall

DOI：10.1021/jo00259a006

日期：1988.11
2-trimethylsilylethyl glycosides. Anomeric deblocking of mono- and disaccharides.

作者：Karl Jansson、Torbjörn Frejd、Jan Kihlberg、Göran Magnusson

DOI：10.1016/s0040-4039(00)80096-9

日期：1988.1
XASEHGAVA, AKIRA;KISO, MAKOTO

作者：XASEHGAVA, AKIRA、KISO, MAKOTO

DOI：——

日期：——