5-Benzyloxy-pentanethioic acid O-{(2S,3R,4aS,6R,7S,8aR)-7-methoxy-6-methoxymethyl-4a-methyl-2-[2-(2-trimethylsilanyl-ethoxythiocarbonyl)-ethyl]-octahydro-pyrano[3,2-b]pyran-3-yl} ester

Base Information

• Chemical Name: 5-Benzyloxy-pentanethioic acid O-{(2S,3R,4aS,6R,7S,8aR)-7-methoxy-6-methoxymethyl-4a-methyl-2-[2-(2-trimethylsilanyl-ethoxythiocarbonyl)-ethyl]-octahydro-pyrano[3,2-b]pyran-3-yl} ester
• CAS No.: 170901-26-5
• Molecular Formula: C₃₂H₅₂O₇S₂Si
• Molecular Weight: 640.978

Synonyms:5-Benzyloxy-pentanethioic acid O-{(2S,3R,4aS,6R,7S,8aR)-7-methoxy-6-methoxymethyl-4a-methyl-2-[2-(2-trimethylsilanyl-ethoxythiocarbonyl)-ethyl]-octahydro-pyrano[3,2-b]pyran-3-yl} ester

Chemical Property of 5-Benzyloxy-pentanethioic acid O-{(2S,3R,4aS,6R,7S,8aR)-7-methoxy-6-methoxymethyl-4a-methyl-2-[2-(2-trimethylsilanyl-ethoxythiocarbonyl)-ethyl]-octahydro-pyrano[3,2-b]pyran-3-yl} ester

Chemical Property:

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Technology Process of 5-Benzyloxy-pentanethioic acid O-{(2S,3R,4aS,6R,7S,8aR)-7-methoxy-6-methoxymethyl-4a-methyl-2-[2-(2-trimethylsilanyl-ethoxythiocarbonyl)-ethyl]-octahydro-pyrano[3,2-b]pyran-3-yl} ester

There total 1 articles about 5-Benzyloxy-pentanethioic acid O-{(2S,3R,4aS,6R,7S,8aR)-7-methoxy-6-methoxymethyl-4a-methyl-2-[2-(2-trimethylsilanyl-ethoxythiocarbonyl)-ethyl]-octahydro-pyrano[3,2-b]pyran-3-yl} ester 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:

5-Benzyloxy-pentanoic acid (2S,3R,4aS,6R,7S,8aR)-7-methoxy-6-methoxymethyl-4a-methyl-2-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-octahydro-pyrano[3,2-b]pyran-3-yl ester → 5-Benzyloxy-pentanethioic acid O-{(2S,3R,4aS,6R,7S,8aR)-7-methoxy-6-methoxymethyl-4a-methyl-2-[2-(2-trimethylsilanyl-ethoxythiocarbonyl)-ethyl]-octahydro-pyrano[3,2-b]pyran-3-yl} ester (170901-26-5)

Guidance literature:

With Lawessons reagent; 1,1,3,3-tetramethyl-2-thiourea; In xylene; at 160 ℃; for 2h;

DOI:10.1021/ja00146a008

Reference yield: 72.0%

5-Benzyloxy-pentanethioic acid O-{(2S,3R,4aS,6R,7S,8aR)-7-methoxy-6-methoxymethyl-4a-methyl-2-[2-(2-trimethylsilanyl-ethoxythiocarbonyl)-ethyl]-octahydro-pyrano[3,2-b]pyran-3-yl} ester (170901-26-5) → {2-[(2R,3S,4aR,5aS,10aR,11aS)-9-(4-Benzyloxy-butyl)-3-methoxy-2-methoxymethyl-11a-methyl-2,3,4,4a,5a,6,7,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yloxy]-ethyl}-trimethyl-silane

Guidance literature:

In benzene; at 70 ℃; for 2h; Irradiation;

DOI:10.1021/ja00146a008

Reference yield:

5-Benzyloxy-pentanethioic acid O-{(2S,3R,4aS,6R,7S,8aR)-7-methoxy-6-methoxymethyl-4a-methyl-2-[2-(2-trimethylsilanyl-ethoxythiocarbonyl)-ethyl]-octahydro-pyrano[3,2-b]pyran-3-yl} ester (170901-26-5) → (2R,3S,4aR,5aS,9S,10aR,11aS)-9-(4-Benzyloxy-butyl)-3-methoxy-2-methoxymethyl-11a-methyl-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-one

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / benzene / 2 h / 70 °C / Irradiation

2: 95 percent / TBAF / tetrahydrofuran / 8 h / 45 °C

With tetrabutyl ammonium fluoride; In tetrahydrofuran; benzene;

DOI:10.1021/ja00146a008

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