(Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-en-1-ol

Base Information

Chemical Name:(Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-en-1-ol
CAS No.:106499-05-2
Molecular Formula:C₂₄H₃₈O₆Si
Molecular Weight:450.648
Hs Code.:

Synonyms:(Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-en-1-ol

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Chemical Property of (Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-en-1-ol

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Technology Process of (Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-en-1-ol

There total 5 articles about (Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-en-1-ol 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: 82.0%

: 106445-06-1
methyl 3-O-benzyl-5-C-tert-butyldimethylsilyloxymethyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-(Z)-enofuranosyluronate

: 106499-05-2
(Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In diethyl ether; at 0 ℃; for 4h;
DOI:10.1139/v86-296

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 106499-05-2
(Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / N,N-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 20 h / Ambient temperature

2: 1) DMSO, trifluoroacetic anhydride, 2) Et₃N / 1) CH₂CL₂, -78 deg C, 15 min, 2) CH₂Cl₂, -78 deg C, 45 min, 3) CH₂Cl₂, -78 deg C, 1 h then RT

3: 84 percent / acetonitrile / 2 h / Heating

4: 82 percent / DIBAL / diethyl ether / 4 h / 0 °C

With dmap; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In diethyl ether; dichloromethane; acetonitrile;
DOI:10.1139/v86-296

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 106499-05-2
(Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / N,N-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 20 h / Ambient temperature

2: 1) DMSO, trifluoroacetic anhydride, 2) Et₃N / 1) CH₂CL₂, -78 deg C, 15 min, 2) CH₂Cl₂, -78 deg C, 45 min, 3) CH₂Cl₂, -78 deg C, 1 h then RT

3: 84 percent / acetonitrile / 2 h / Heating

4: 82 percent / DIBAL / diethyl ether / 4 h / 0 °C

With dmap; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In diethyl ether; dichloromethane; acetonitrile;
DOI:10.1139/v86-296