(2R,3S,4R,6R)-2-Benzyloxy-4-methyl-3,6-bis-triethylsilanyloxy-heptanethioic acid S-ethyl ester

Base Information

Chemical Name:(2R,3S,4R,6R)-2-Benzyloxy-4-methyl-3,6-bis-triethylsilanyloxy-heptanethioic acid S-ethyl ester
CAS No.:681830-34-2
Molecular Formula:C₂₉H₅₄O₄SSi₂
Molecular Weight:554.982
Hs Code.:

Synonyms:(2R,3S,4R,6R)-2-Benzyloxy-4-methyl-3,6-bis-triethylsilanyloxy-heptanethioic acid S-ethyl ester

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Chemical Property of (2R,3S,4R,6R)-2-Benzyloxy-4-methyl-3,6-bis-triethylsilanyloxy-heptanethioic acid S-ethyl ester

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Technology Process of (2R,3S,4R,6R)-2-Benzyloxy-4-methyl-3,6-bis-triethylsilanyloxy-heptanethioic acid S-ethyl ester

There total 7 articles about (2R,3S,4R,6R)-2-Benzyloxy-4-methyl-3,6-bis-triethylsilanyloxy-heptanethioic acid S-ethyl 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: 89.0%

: 75-08-1
ethanethiol

: 681830-31-9
(R)-4-Benzyl-3-((2R,3S,4R,6R)-2-benzyloxy-4-methyl-3,6-bis-triethylsilanyloxy-heptanoyl)-oxazolidin-2-one

: 681830-34-2
(2R,3S,4R,6R)-2-Benzyloxy-4-methyl-3,6-bis-triethylsilanyloxy-heptanethioic acid S-ethyl ester

Guidance literature:: With potassium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 2.33333h;
DOI:10.1021/jo035829l

Reference yield:

: 994-30-9
triethylsilyl chloride

: 681830-34-2
(2R,3S,4R,6R)-2-Benzyloxy-4-methyl-3,6-bis-triethylsilanyloxy-heptanethioic acid S-ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 °C

2.1: 78 percent / diisopropylamine; n-BuLi; BH₃*NH₃ / tetrahydrofuran; hexane / 12 h / 0 - 20 °C

3.1: 85 percent / NMO / TPAP / CH₂Cl₂ / 0.5 h

4.1: Bu₂BOTf; Et₃N / toluene / 1.5 h / -50 °C

4.2: toluene / 2.17 h / -50 - -30 °C

5.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

6.1: 89 percent / KH / tetrahydrofuran / 2.33 h / 0 - 20 °C

With 2,6-dimethylpyridine; dmap; n-butyllithium; borane-ammonia complex; N-methyl-2-indolinone; di-n-butylboryl trifluoromethanesulfonate; potassium hydride; triethylamine; diisopropylamine; tetrapropylammonium perruthennate; In tetrahydrofuran; hexane; dichloromethane; toluene; 3.1: Ley oxidation;
DOI:10.1021/jo035829l

Reference yield:

: 681830-33-1
(2R,4R)-2-methyl-4-(trimethylsilyloxy)pentan-1-ol

: 681830-34-2
(2R,3S,4R,6R)-2-Benzyloxy-4-methyl-3,6-bis-triethylsilanyloxy-heptanethioic acid S-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 85 percent / NMO / TPAP / CH₂Cl₂ / 0.5 h

2.1: Bu₂BOTf; Et₃N / toluene / 1.5 h / -50 °C

2.2: toluene / 2.17 h / -50 - -30 °C

3.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

4.1: 89 percent / KH / tetrahydrofuran / 2.33 h / 0 - 20 °C

With 2,6-dimethylpyridine; N-methyl-2-indolinone; di-n-butylboryl trifluoromethanesulfonate; potassium hydride; triethylamine; tetrapropylammonium perruthennate; In tetrahydrofuran; dichloromethane; toluene; 1.1: Ley oxidation;
DOI:10.1021/jo035829l