(2S,3R,6R,7R,8S,10S,11R)-3-(benzyloxy)-6,7,10,11-tetrachloro-11-((2S,3S)-3-(hydroxylmethyl)oxiran-2-yl)undecane-2,8-diol

Base Information

• Chemical Name: (2S,3R,6R,7R,8S,10S,11R)-3-(benzyloxy)-6,7,10,11-tetrachloro-11-((2S,3S)-3-(hydroxylmethyl)oxiran-2-yl)undecane-2,8-diol
• CAS No.: 1333237-19-6
• Molecular Formula: C₂₁H₃₀Cl₄O₅
• Molecular Weight: 504.278

Synonyms:(2S,3R,6R,7R,8S,10S,11R)-3-(benzyloxy)-6,7,10,11-tetrachloro-11-((2S,3S)-3-(hydroxylmethyl)oxiran-2-yl)undecane-2,8-diol

Chemical Property of (2S,3R,6R,7R,8S,10S,11R)-3-(benzyloxy)-6,7,10,11-tetrachloro-11-((2S,3S)-3-(hydroxylmethyl)oxiran-2-yl)undecane-2,8-diol

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Technology Process of (2S,3R,6R,7R,8S,10S,11R)-3-(benzyloxy)-6,7,10,11-tetrachloro-11-((2S,3S)-3-(hydroxylmethyl)oxiran-2-yl)undecane-2,8-diol

There total 2 articles about (2S,3R,6R,7R,8S,10S,11R)-3-(benzyloxy)-6,7,10,11-tetrachloro-11-((2S,3S)-3-(hydroxylmethyl)oxiran-2-yl)undecane-2,8-diol 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%

((2S,3S)-3-((1R,2S,4S,5R,6R,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methanol (1333237-06-1) → (2S,3R,6R,7R,8S,10S,11R)-3-(benzyloxy)-6,7,10,11-tetrachloro-11-((2S,3S)-3-(hydroxylmethyl)oxiran-2-yl)undecane-2,8-diol (1333237-19-6)

Guidance literature:

With pyridine; pyridine hydrofluoride; In acetonitrile; at 0 - 20 ℃; for 45h; Inert atmosphere;

DOI:10.1002/anie.201102521

Reference yield:

((2S,3S)-3-((1R,2S,4S,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methyl acetate → (2S,3R,6R,7R,8S,10S,11R)-3-(benzyloxy)-6,7,10,11-tetrachloro-11-((2S,3S)-3-(hydroxylmethyl)oxiran-2-yl)undecane-2,8-diol (1333237-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; potassium carbonate / 0.17 h / 0 °C / Inert atmosphere

2: pyridine; pyridine hydrofluoride / acetonitrile / 45 h / 0 - 20 °C / Inert atmosphere

With pyridine; methanol; pyridine hydrofluoride; potassium carbonate; In acetonitrile;

DOI:10.1002/anie.201102521

Reference yield: 64.0%

(2S,3R,6R,7R,8S,10S,11R)-3-(benzyloxy)-6,7,10,11-tetrachloro-11-((2S,3S)-3-(hydroxylmethyl)oxiran-2-yl)undecane-2,8-diol (1333237-19-6) + t-butyldimethylsiyl triflate (69739-34-0) → (1R,2S,4S,5R,6R,9R,10S)-9-(benzyloxy)-10-(tert-butyldimethylsilyloxy)-1-((2S,3S)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-1,2,5,6-tetrachloroundecan-4-ol (1333237-20-9)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 - -40 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/anie.201102521

upstream raw materials:

((2S,3S)-3-((1R,2S,4S,5R,6R,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methanol

Downstream raw materials:

(((2S,3S)-3-((E)-3-((2S,3S)-3-((1R,4R,5S)-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-1-chlorohexyl)oxiran-2-yl)-1-chloroprop-1-enyl)oxiran-2-yl)methoxy)(tert-butyl)dimethylsilane

(1E,4S,5Z,9R,10S)-9-(benzyloxy)-10-(tert-butyldimethylsilyloxy)-1-((2S,3S)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-1,5-dichloroundeca-1,5-dien-4-ol

(1R,2S,4S,5R,6R,9R,10S)-9-(benzyloxy)-10-(tert-butyldimethylsilyloxy)-1-((2S,3S)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-1,2,5,6-tetrachloroundecan-4-ol

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