(2S,3R,4S)-3-benzyloxymethoxy-2,4-dimethyl-4-[(1R,2R,3S,4R)-3,4-di(tert-butyldimethylsiloxy)-1-hydroxy-2-methylpentan-1-yl]butanolide

Base Information

Chemical Name:(2S,3R,4S)-3-benzyloxymethoxy-2,4-dimethyl-4-[(1R,2R,3S,4R)-3,4-di(tert-butyldimethylsiloxy)-1-hydroxy-2-methylpentan-1-yl]butanolide
CAS No.:916321-14-7
Molecular Formula:C₃₂H₅₈O₇Si₂
Molecular Weight:610.979
Hs Code.:

Synonyms:(2S,3R,4S)-3-benzyloxymethoxy-2,4-dimethyl-4-[(1R,2R,3S,4R)-3,4-di(tert-butyldimethylsiloxy)-1-hydroxy-2-methylpentan-1-yl]butanolide

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Chemical Property of (2S,3R,4S)-3-benzyloxymethoxy-2,4-dimethyl-4-[(1R,2R,3S,4R)-3,4-di(tert-butyldimethylsiloxy)-1-hydroxy-2-methylpentan-1-yl]butanolide

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Technology Process of (2S,3R,4S)-3-benzyloxymethoxy-2,4-dimethyl-4-[(1R,2R,3S,4R)-3,4-di(tert-butyldimethylsiloxy)-1-hydroxy-2-methylpentan-1-yl]butanolide

There total 11 articles about (2S,3R,4S)-3-benzyloxymethoxy-2,4-dimethyl-4-[(1R,2R,3S,4R)-3,4-di(tert-butyldimethylsiloxy)-1-hydroxy-2-methylpentan-1-yl]butanolide 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: 17.0%

: 916321-38-5
S-ethyl (E)-(2S,3R,6S,7R,8R)-3-(benzyloxymethoxy)-7,8-di(tert-butyldimethylsiloxy)-2,4,6-trimethyl-4-nonenethioate

: 916321-37-4
(2S,3R,4R)-3-benzyloxymethoxy-2,4-dimethyl-4-[(1S,2R,3S,4R)-3,4-di(tert-butyldimethylsiloxy)-1-hydroxy-2-methylpentan-1-yl]butanolide

: 916321-14-7
(2S,3R,4S)-3-benzyloxymethoxy-2,4-dimethyl-4-[(1R,2R,3S,4R)-3,4-di(tert-butyldimethylsiloxy)-1-hydroxy-2-methylpentan-1-yl]butanolide

Guidance literature:: S-ethyl (E)-(2S,3R,6S,7R,8R)-3-(benzyloxymethoxy)-7,8-di(tert-butyldimethylsiloxy)-2,4,6-trimethyl-4-nonenethioate; With osmium(VIII) oxide; In pyridine; at 0 ℃; for 30h;

With hydrogen sulfide; In tetrahydrofuran; hexane;
DOI:10.1021/ol062058+

Reference yield:

: 916321-09-0
S-ethyll (2S,3S,4R)-4-(tert-butyldimethylsiloxy)-3-hydroxy-2-methylpentanethioate

: 916321-14-7
(2S,3R,4S)-3-benzyloxymethoxy-2,4-dimethyl-4-[(1R,2R,3S,4R)-3,4-di(tert-butyldimethylsiloxy)-1-hydroxy-2-methylpentan-1-yl]butanolide

Guidance literature:: Multi-step reaction with 8 steps

1.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

2.1: 100 percent / Et₃SiH / Pd/C / acetone / 1.5 h / 0 °C

3.1: 95 percent / toluene / 6.5 h / 100 °C

4.1: 92 percent / L-Selectride(R) / tetrahydrofuran / 5 h / 20 °C

5.1: 100 percent / NMO; TPAP / CH₂Cl₂ / 2 h / 0 °C

6.1: 49.9 percent / tetrahydrofuran / 3 h / -78 °C

7.1: 96 percent / iPr₂NEt / CH₂Cl₂ / 11 h / 60 °C

8.1: OsO₄ / pyridine / 30 h / 0 °C

8.2: 17 percent / H₂S / tetrahydrofuran; hexane

With 2,6-dimethylpyridine; triethylsilane; osmium(VIII) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; L-Selectride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; dichloromethane; acetone; toluene; 3.1: Wittig reaction;
DOI:10.1021/ol062058+

Reference yield:

: 916321-31-8
S-ethyll (2S,3S,4R)-3,4-di(tert-butyldimethylsiloxy)-2-methylpentanethioate

: 916321-14-7
(2S,3R,4S)-3-benzyloxymethoxy-2,4-dimethyl-4-[(1R,2R,3S,4R)-3,4-di(tert-butyldimethylsiloxy)-1-hydroxy-2-methylpentan-1-yl]butanolide

Guidance literature:: Multi-step reaction with 7 steps

1.1: 100 percent / Et₃SiH / Pd/C / acetone / 1.5 h / 0 °C

2.1: 95 percent / toluene / 6.5 h / 100 °C

3.1: 92 percent / L-Selectride(R) / tetrahydrofuran / 5 h / 20 °C

4.1: 100 percent / NMO; TPAP / CH₂Cl₂ / 2 h / 0 °C

5.1: 49.9 percent / tetrahydrofuran / 3 h / -78 °C

6.1: 96 percent / iPr₂NEt / CH₂Cl₂ / 11 h / 60 °C

7.1: OsO₄ / pyridine / 30 h / 0 °C

7.2: 17 percent / H₂S / tetrahydrofuran; hexane

With triethylsilane; osmium(VIII) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; L-Selectride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; dichloromethane; acetone; toluene; 2.1: Wittig reaction;
DOI:10.1021/ol062058+