(R)-4-[(R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolane-2-thione

Base Information

Chemical Name:(R)-4-[(R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolane-2-thione
CAS No.:106445-11-8
Molecular Formula:C₂₅H₃₈O₇SSi
Molecular Weight:510.724
Hs Code.:

(R)-4-[(R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolane-2-thione

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

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

There total 7 articles about (R)-4-[(R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolane-2-thione 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: 90.0%

: 94393-43-8
(2R,3R)-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)-butane-1,2-diol

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 106445-11-8
(R)-4-[(R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolane-2-thione

Guidance literature:: In tetrahydrofuran; for 1h; Heating;
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

: 106445-11-8
(R)-4-[(R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolane-2-thione

Guidance literature:: Multi-step reaction with 6 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

4: DIBAL / diethyl ether / 4 h / 0 °C

5: 1) diborane, 2) 3N NaOH, 30percent H₂O₂ / 1) THF, 0 deg C, 6 h, 2) THF, RT, 3 h

6: 90 percent / tetrahydrofuran / 1 h / Heating

With dmap; sodium hydroxide; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; diborane; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1139/v86-296

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 106445-11-8
(R)-4-[(R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolane-2-thione

Guidance literature:: Multi-step reaction with 6 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

4: DIBAL / diethyl ether / 4 h / 0 °C

5: 1) diborane, 2) 3N NaOH, 30percent H₂O₂ / 1) THF, 0 deg C, 6 h, 2) THF, RT, 3 h

6: 90 percent / tetrahydrofuran / 1 h / Heating

With dmap; sodium hydroxide; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; diborane; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1139/v86-296