(S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-hydroxy-butyric acid methyl ester

Base Information

Chemical Name:(S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-hydroxy-butyric acid methyl ester
CAS No.:106445-08-3
Molecular Formula:C₁₉H₂₆O₇
Molecular Weight:366.411
Hs Code.:

Synonyms:(S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-hydroxy-butyric acid methyl ester

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Chemical Property of (S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-hydroxy-butyric acid methyl ester

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Technology Process of (S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-hydroxy-butyric acid methyl ester

There total 5 articles about (S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-hydroxy-butyric acid methyl 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:

: (Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-hydroxy-but-2-enoic acid methyl ester

: 106445-09-4
(S)-4-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-dihydro-furan-2-one

: 106445-08-3
(S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-hydroxy-butyric acid methyl ester

Guidance literature:: With hydrogen; platinum on activated charcoal; In benzene; for 0.75h; under 25857.4 Torr; Title compound not separated from byproducts;
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

: 106445-08-3
(S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-hydroxy-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 5 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: NH₄F / methanol; H₂O / 3 h / Heating

5: hydrogen / 5percent Pt/C / benzene / 0.75 h / 25857.4 Torr

With dmap; ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; platinum on activated charcoal; In methanol; dichloromethane; water; acetonitrile; benzene;
DOI:10.1139/v86-296

Reference yield:

: 106445-04-9
1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol

: 106445-08-3
(S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-hydroxy-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 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

2: 84 percent / acetonitrile / 2 h / Heating

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

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

With ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; platinum on activated charcoal; In methanol; water; acetonitrile; benzene;
DOI:10.1139/v86-296