(2R,3S,4S)-(Z)-1-O-(t-butyldimethylsilyl)-2,7-di-O-benzyl-4,5-isopropylidenehept-2-ene-1,2,3,4,7-pentol

Base Information

Chemical Name:(2R,3S,4S)-(Z)-1-O-(t-butyldimethylsilyl)-2,7-di-O-benzyl-4,5-isopropylidenehept-2-ene-1,2,3,4,7-pentol
CAS No.:197716-22-6
Molecular Formula:C₃₀H₄₄O₅Si
Molecular Weight:512.762
Hs Code.:

Synonyms:(2R,3S,4S)-(Z)-1-O-(t-butyldimethylsilyl)-2,7-di-O-benzyl-4,5-isopropylidenehept-2-ene-1,2,3,4,7-pentol

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Chemical Property of (2R,3S,4S)-(Z)-1-O-(t-butyldimethylsilyl)-2,7-di-O-benzyl-4,5-isopropylidenehept-2-ene-1,2,3,4,7-pentol

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Technology Process of (2R,3S,4S)-(Z)-1-O-(t-butyldimethylsilyl)-2,7-di-O-benzyl-4,5-isopropylidenehept-2-ene-1,2,3,4,7-pentol

There total 5 articles about (2R,3S,4S)-(Z)-1-O-(t-butyldimethylsilyl)-2,7-di-O-benzyl-4,5-isopropylidenehept-2-ene-1,2,3,4,7-pentol 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:

: 100-44-7
benzyl chloride

: 260416-02-2
(Z)-3-{(4S,5R)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenol

: 197716-22-6
(2R,3S,4S)-(Z)-1-O-(t-butyldimethylsilyl)-2,7-di-O-benzyl-4,5-isopropylidenehept-2-ene-1,2,3,4,7-pentol

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; Yield given; 1.) 0 deg C, 2.) 0 deg C to r.t.;

Reference yield:

: 217309-46-1
5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose

: 197716-22-6
(2R,3S,4S)-(Z)-1-O-(t-butyldimethylsilyl)-2,7-di-O-benzyl-4,5-isopropylidenehept-2-ene-1,2,3,4,7-pentol

Guidance literature:: Multi-step reaction with 5 steps

1: 3.152 g / PhCO₂H / CH₂Cl₂ / 36 h / Heating

2: 97 percent / PPTS / CH₂Cl₂ / 24 h / 20 °C

3: 1.777 g / DIBALH / diethyl ether / 3 h / 0 °C

4: MgBr₂ / diethyl ether; benzene / 12 h / 20 °C

5: 1.340 g / NaH / dimethylformamide / 14 h / 0 - 20 °C

With pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; benzoic acid; magnesium bromide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Wittig olefination / 2: Etherification / 3: Reduction / 4: Hydrolysis / 5: Etherification;
DOI:10.1016/S0040-4020(99)00991-6

Reference yield:

: 197716-19-1
methyl (4S,5S,6R)-(Z)-6-hydroxy-7-t-butyldimethylsilyloxy-4,5-isopropylidenedioxyhept-2-enoate

: 197716-22-6
(2R,3S,4S)-(Z)-1-O-(t-butyldimethylsilyl)-2,7-di-O-benzyl-4,5-isopropylidenehept-2-ene-1,2,3,4,7-pentol

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / PPTS / CH₂Cl₂ / 24 h / 20 °C

2: 1.777 g / DIBALH / diethyl ether / 3 h / 0 °C

3: MgBr₂ / diethyl ether; benzene / 12 h / 20 °C

4: 1.340 g / NaH / dimethylformamide / 14 h / 0 - 20 °C

With pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; magnesium bromide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Etherification / 2: Reduction / 3: Hydrolysis / 4: Etherification;
DOI:10.1016/S0040-4020(99)00991-6