(2R,3S,4S,5S,6R,7S)-4-Benzyloxy-7-methoxymethoxymethyl-5-methyl-2-((S)-1-methyl-allyl)-6-triisopropylsilanyloxy-oxepan-3-ol

Base Information

Chemical Name:(2R,3S,4S,5S,6R,7S)-4-Benzyloxy-7-methoxymethoxymethyl-5-methyl-2-((S)-1-methyl-allyl)-6-triisopropylsilanyloxy-oxepan-3-ol
CAS No.:157220-15-0
Molecular Formula:C₃₀H₅₂O₆Si
Molecular Weight:536.825
Hs Code.:

Synonyms:(2R,3S,4S,5S,6R,7S)-4-Benzyloxy-7-methoxymethoxymethyl-5-methyl-2-((S)-1-methyl-allyl)-6-triisopropylsilanyloxy-oxepan-3-ol

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Chemical Property of (2R,3S,4S,5S,6R,7S)-4-Benzyloxy-7-methoxymethoxymethyl-5-methyl-2-((S)-1-methyl-allyl)-6-triisopropylsilanyloxy-oxepan-3-ol

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Technology Process of (2R,3S,4S,5S,6R,7S)-4-Benzyloxy-7-methoxymethoxymethyl-5-methyl-2-((S)-1-methyl-allyl)-6-triisopropylsilanyloxy-oxepan-3-ol

There total 5 articles about (2R,3S,4S,5S,6R,7S)-4-Benzyloxy-7-methoxymethoxymethyl-5-methyl-2-((S)-1-methyl-allyl)-6-triisopropylsilanyloxy-oxepan-3-ol 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: 71.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: (3R,3aR,5S,6R,7S,8S,8aS)-8-Benzyloxy-5-methoxymethoxymethyl-3,7-dimethyl-6-triisopropylsilanyloxy-octahydro-furo[3,2-b]oxepin-2-ol

: 157220-15-0
(2R,3S,4S,5S,6R,7S)-4-Benzyloxy-7-methoxymethoxymethyl-5-methyl-2-((S)-1-methyl-allyl)-6-triisopropylsilanyloxy-oxepan-3-ol

Guidance literature:: Methyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.5h;

(3R,3aR,5S,6R,7S,8S,8aS)-8-Benzyloxy-5-methoxymethoxymethyl-3,7-dimethyl-6-triisopropylsilanyloxy-octahydro-furo[3,2-b]oxepin-2-ol; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1021/jo990988j

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 157220-15-0
(2R,3S,4S,5S,6R,7S)-4-Benzyloxy-7-methoxymethoxymethyl-5-methyl-2-((S)-1-methyl-allyl)-6-triisopropylsilanyloxy-oxepan-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium dimsylate / tetrahydrofuran; dimethylsulfoxide / 0 - 20 °C

1.2: 16.64 g / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

2.1: [Ir(COD)(Ph₂MeP)2]PF₆; hydrogen / tetrahydrofuran / 0.58 h / 20 °C

2.2: 9.69 g / iodine / tetrahydrofuran; H₂O / 0.08 h / 20 °C

3.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

3.2: 71 percent / tetrahydrofuran / 0 - 20 °C

With (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen; sodium hexamethyldisilazane; potassium dimsylate; In tetrahydrofuran; dimethyl sulfoxide; 1.1: Cyclization / 1.2: Etherification / 2.1: Hydrolysis / 2.2: Hydrolysis / 3.1: Dehydrobromination / 3.2: methylenation; Wittig reaction;
DOI:10.1021/jo990988j

Reference yield:

: (2R,3R,4R)-5-Allyloxy-2-[(1S,2S)-1-benzyloxy-2-((2R,3R)-3-methoxymethoxymethyl-oxiranyl)-propyl]-4-methyl-tetrahydro-furan-3-ol

: 157220-15-0
(2R,3S,4S,5S,6R,7S)-4-Benzyloxy-7-methoxymethoxymethyl-5-methyl-2-((S)-1-methyl-allyl)-6-triisopropylsilanyloxy-oxepan-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium dimsylate / tetrahydrofuran; dimethylsulfoxide / 0 - 20 °C

1.2: 16.64 g / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

2.1: [Ir(COD)(Ph₂MeP)2]PF₆; hydrogen / tetrahydrofuran / 0.58 h / 20 °C

2.2: 9.69 g / iodine / tetrahydrofuran; H₂O / 0.08 h / 20 °C

3.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

3.2: 71 percent / tetrahydrofuran / 0 - 20 °C

With (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen; sodium hexamethyldisilazane; potassium dimsylate; In tetrahydrofuran; dimethyl sulfoxide; 1.1: Cyclization / 1.2: Etherification / 2.1: Hydrolysis / 2.2: Hydrolysis / 3.1: Dehydrobromination / 3.2: methylenation; Wittig reaction;
DOI:10.1021/jo990988j