(2S,3R,4S,5S,6E)-5-benzyloxy-1-((4S)-4-benzyl-2-thioxooxazolidin-3-yl)-3-hydroxy-2,4-dimethyl-8-(4-methoxybenzyloxy)oct-6-en-1-one

Base Information

• Chemical Name: (2S,3R,4S,5S,6E)-5-benzyloxy-1-((4S)-4-benzyl-2-thioxooxazolidin-3-yl)-3-hydroxy-2,4-dimethyl-8-(4-methoxybenzyloxy)oct-6-en-1-one
• CAS No.: 1199613-18-7
• Molecular Formula: C₃₅H₄₁NO₆S
• Molecular Weight: 603.78

Synonyms:(2S,3R,4S,5S,6E)-5-benzyloxy-1-((4S)-4-benzyl-2-thioxooxazolidin-3-yl)-3-hydroxy-2,4-dimethyl-8-(4-methoxybenzyloxy)oct-6-en-1-one

Chemical Property of (2S,3R,4S,5S,6E)-5-benzyloxy-1-((4S)-4-benzyl-2-thioxooxazolidin-3-yl)-3-hydroxy-2,4-dimethyl-8-(4-methoxybenzyloxy)oct-6-en-1-one

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Technology Process of (2S,3R,4S,5S,6E)-5-benzyloxy-1-((4S)-4-benzyl-2-thioxooxazolidin-3-yl)-3-hydroxy-2,4-dimethyl-8-(4-methoxybenzyloxy)oct-6-en-1-one

There total 1 articles about (2S,3R,4S,5S,6E)-5-benzyloxy-1-((4S)-4-benzyl-2-thioxooxazolidin-3-yl)-3-hydroxy-2,4-dimethyl-8-(4-methoxybenzyloxy)oct-6-en-1-one 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: 94.0%

C22H26O4 + N-propanoyl-(S)-4-benzyl-1,3-oxazolidine-2-thione (145588-95-0,334968-78-4) → (2S,3R,4S,5S,6E)-5-benzyloxy-1-((4S)-4-benzyl-2-thioxooxazolidin-3-yl)-3-hydroxy-2,4-dimethyl-8-(4-methoxybenzyloxy)oct-6-en-1-one (1199613-18-7)

Guidance literature:

N-propanoyl-(S)-4-benzyl-1,3-oxazolidine-2-thione; With titanium tetrachloride; In dichloromethane; at 0 ℃; Inert atmosphere;

With (-)-sparteine; In dichloromethane; at 0 ℃; Inert atmosphere;

C₂₂H₂₆O₄; diastereoselective reaction; Further stages;

DOI:10.1021/jo100774n

Reference yield: 90.0%

chloro-trimethyl-silane (75-77-4) + (2S,3R,4S,5S,6E)-5-benzyloxy-1-((4S)-4-benzyl-2-thioxooxazolidin-3-yl)-3-hydroxy-2,4-dimethyl-8-(4-methoxybenzyloxy)oct-6-en-1-one (1199613-18-7) → C38H49NO6SSi

Guidance literature:

With 2,6-dimethylpyridine; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo100774n

Reference yield: 70.0%

methanol (67-56-1) + (2S,3R,4S,5S,6E)-5-benzyloxy-1-((4S)-4-benzyl-2-thioxooxazolidin-3-yl)-3-hydroxy-2,4-dimethyl-8-(4-methoxybenzyloxy)oct-6-en-1-one (1199613-18-7) → methyl (2S,3R,4S,5S,6E)-5-benzyloxy-3-hydroxy-8-(4-methoxybenzyloxy)-2,4-dimethyloct-6-enate (1236299-80-1)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃;

DOI:10.1021/jo100774n

upstream raw materials:

N-propanoyl-(S)-4-benzyl-1,3-oxazolidine-2-thione

Downstream raw materials:

methyl (2S,3R,4S,5S,6E)-5-benzyloxy-3-hydroxy-8-(4-methoxybenzyloxy)-2,4-dimethyloct-6-enate

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