(4R,5R,6S)-1-<(tert-butyldimethylsilyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-hepten-6-ol

Base Information

Chemical Name:(4R,5R,6S)-1-<(tert-butyldimethylsilyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-hepten-6-ol
CAS No.:173142-25-1
Molecular Formula:C₃₄H₄₆O₅Si
Molecular Weight:562.822
Hs Code.:

Synonyms:(4R,5R,6S)-1-<(tert-butyldimethylsilyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-hepten-6-ol

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Chemical Property of (4R,5R,6S)-1-<(tert-butyldimethylsilyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-hepten-6-ol

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Technology Process of (4R,5R,6S)-1-<(tert-butyldimethylsilyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-hepten-6-ol

There total 8 articles about (4R,5R,6S)-1-<(tert-butyldimethylsilyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-hepten-6-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: 96.0%

: 172986-76-4
(4R,5R,6S)-6-acetoxy-1-<(tert-butyldimethylsilyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-heptene

: 173142-25-1
(4R,5R,6S)-1-<(tert-butyldimethylsilyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-hepten-6-ol

Guidance literature:: With sodium methylate; In methanol; for 1h; Ambient temperature;
DOI:10.1021/jo9902446

Reference yield:

: 146346-44-3
methyl (4R,5R,6R)-6-hydroxy-4,5,7-tris(benzyloxy)-2(E)-heptenoate

: 173142-25-1
(4R,5R,6S)-1-<(tert-butyldimethylsilyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-hepten-6-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 96.5 percent / DIBAL / CH₂Cl₂ / 1.5 h / 0 °C

2: 95 percent / Et₃N, DMAP / dimethylformamide / 1 h / Ambient temperature

3: 98 percent / pyridine / 0.5 h / Ambient temperature

4: 92 percent / 18-crown-6 / toluene / 12 h / Heating

5: 96 percent / NaOMe / methanol / 1 h / Ambient temperature

With dmap; 18-crown-6 ether; sodium methylate; diisobutylaluminium hydride; triethylamine; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo9902446

Reference yield:

: 231618-83-0
(4R,5R,6R)-4,5,7-tris(benzyloxy)-2(E)-heptene-1,6-diol

: 173142-25-1
(4R,5R,6S)-1-<(tert-butyldimethylsilyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-hepten-6-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / Et₃N, DMAP / dimethylformamide / 1 h / Ambient temperature

2: 98 percent / pyridine / 0.5 h / Ambient temperature

3: 92 percent / 18-crown-6 / toluene / 12 h / Heating

4: 96 percent / NaOMe / methanol / 1 h / Ambient temperature

With dmap; 18-crown-6 ether; sodium methylate; triethylamine; In pyridine; methanol; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo9902446