1-[(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-one

Base Information

Chemical Name:1-[(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-one
CAS No.:1391973-94-6
Molecular Formula:C₄₁H₆₄O₈Si₂
Molecular Weight:741.125
Hs Code.:

1-[(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-one

Synonyms:1-[(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-one

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Chemical Property of 1-[(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-one

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Technology Process of 1-[(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-one

There total 11 articles about 1-[(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

: 1391973-93-5
(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide

: 1826-67-1
vinyl magnesium bromide

: 1391973-94-6
1-[(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-one

: 1391974-10-9
1-[(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]-3-[methoxy(methyl)amino]propan-1-one

Guidance literature:: In tetrahydrofuran; at 10 - 20 ℃; for 0.666667h; Inert atmosphere;
DOI:10.1002/anie.201201826

Reference yield: 56.0%

: 1391974-10-9
1-[(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]-3-[methoxy(methyl)amino]propan-1-one

: 1391973-94-6
1-[(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-one

Guidance literature:: With N-ethyl-N,N-diisopropylamine; methyl iodide; In tetrahydrofuran; at 50 ℃; for 168h; Inert atmosphere;
DOI:10.1021/jo401706r

Reference yield:

: methyl 5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolane-4-carboxylate

: 1391973-94-6
1-[(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 0.58 h / 20 °C

2.1: 1,1'-carbonyldiimidazole / dichloromethane / 20 °C / Inert atmosphere

2.2: 4 h / 20 °C / Inert atmosphere

3.1: tetrahydrofuran / -10 - 20 °C / Inert atmosphere

With lithium hydroxide monohydrate; water; 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo401706r