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

Base Information

• Chemical Name: (4R,5R,6S)-1-<(tert-butyldimethylsilyl)oxy>-6-<((chloromethyl)sulfonyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-heptene
• CAS No.: 231618-85-2
• Molecular Formula: C₃₅H₄₇ClO₇SSi
• Molecular Weight: 675.358
• Mol file: 231618-85-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (4R,5R,6S)-1-<(tert-butyldimethylsilyl)oxy>-6-<((chloromethyl)sulfonyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-heptene 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: 92.0%

monochloromethanesulfonyl chloride (3518-65-8) + (4R,5R,6S)-1-<(tert-butyldimethylsilyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-hepten-6-ol (173142-25-1) → (4R,5R,6S)-1-<(tert-butyldimethylsilyl)oxy>-6-<((chloromethyl)sulfonyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-heptene (231618-85-2)

Guidance literature:

In pyridine; for 0.5h; Ambient temperature;

DOI:10.1021/jo9902446

Reference yield:

methyl (4R,5R,6R)-6-hydroxy-4,5,7-tris(benzyloxy)-2(E)-heptenoate (146346-44-3) → (4R,5R,6S)-1-<(tert-butyldimethylsilyl)oxy>-6-<((chloromethyl)sulfonyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-heptene (231618-85-2)

Guidance literature:

Multi-step reaction with 6 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

6: 92 percent / pyridine / 0.5 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:

(4R,5R,6S)-6-acetoxy-1-<(tert-butyldimethylsilyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-heptene (172986-76-4) → (4R,5R,6S)-1-<(tert-butyldimethylsilyl)oxy>-6-<((chloromethyl)sulfonyl)oxy>-4,5,7-tris(benzyloxy)-2(E)-heptene (231618-85-2)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 92 percent / pyridine / 0.5 h / Ambient temperature

With sodium methylate; In pyridine; methanol;

DOI:10.1021/jo9902446

upstream raw materials:

monochloromethanesulfonyl chloride

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

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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

(2S,3R,4S,5R,6S)-6-<((chloromethyl)sulfonyl)oxy>-2,3-epoxy-4,5,7-tris(benzyloxy)-2(E)-hepten-1-ol

(2R,3S,4S,5R,6S)-6-<((chloromethyl)sulfonyl)oxy>-2,3-epoxy-4,5,7-tris(benzyloxy)-2(E)-hepten-1-ol