Benzoic acid (3aR,5R,6S,6aR)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Base Information

Chemical Name:Benzoic acid (3aR,5R,6S,6aR)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
CAS No.:99665-46-0
Molecular Formula:C₂₂H₃₄O₇Si
Molecular Weight:438.593
Hs Code.:

Synonyms:Benzoic acid (3aR,5R,6S,6aR)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

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Chemical Property of Benzoic acid (3aR,5R,6S,6aR)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

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Technology Process of Benzoic acid (3aR,5R,6S,6aR)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

There total 1 articles about Benzoic acid (3aR,5R,6S,6aR)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 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: 80.0%

: 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

: 18162-48-6
tert-butyldimethylsilyl chloride

: 99665-46-0
Benzoic acid (3aR,5R,6S,6aR)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Guidance literature:: With pyridine; for 1h;
DOI:10.1021/jo00350a062

Reference yield:

: 99665-46-0
Benzoic acid (3aR,5R,6S,6aR)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

: 94744-86-2
Benzoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-((R)-5-oxo-tetrahydro-furan-3-yl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) CrO₃, pyridine, 2.) Ac₂O / 1.) CH₂Cl₂, 5 min, 2.) CH₂Cl₂, 1 h

2: 41 percent / acetonitrile / 2 h / Heating

3: 81 percent / NH₄F / H₂O; methanol / 3 h / Heating

4: 1.) H₂, 2.) p-toluenesulfonic acid / 1.) 5percent Pt/C / 1.) C₆H₆, 500 psi, 45 min, 2.) 23 deg C, 6 h

With pyridine; chromium(VI) oxide; ammonium fluoride; hydrogen; acetic anhydride; toluene-4-sulfonic acid; platinum on activated charcoal; In methanol; water; acetonitrile;
DOI:10.1021/jo00350a062

Reference yield:

: 99665-46-0
Benzoic acid (3aR,5R,6S,6aR)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

: Benzoic acid (3aR,5R,6S,6aR)-5-((R)-2-ethoxycarbonyl-1-hydroxymethyl-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) CrO₃, pyridine, 2.) Ac₂O / 1.) CH₂Cl₂, 5 min, 2.) CH₂Cl₂, 1 h

2: 41 percent / acetonitrile / 2 h / Heating

3: 81 percent / NH₄F / H₂O; methanol / 3 h / Heating

4: H₂ / 5percent Pt/C / benzene / 0.75 h / 25857.4 Torr

With pyridine; chromium(VI) oxide; ammonium fluoride; hydrogen; acetic anhydride; platinum on activated charcoal; In methanol; water; acetonitrile; benzene;
DOI:10.1021/jo00350a062