(2S,3R,5R,7S,8R)-3-Benzyloxy-2-benzyloxymethyl-8-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-5-methyl-7-(naphthalen-2-ylmethoxy)-oxocane

Base Information

Chemical Name:(2S,3R,5R,7S,8R)-3-Benzyloxy-2-benzyloxymethyl-8-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-5-methyl-7-(naphthalen-2-ylmethoxy)-oxocane
CAS No.:871912-49-1
Molecular Formula:C₃₈H₄₆O₅S₂
Molecular Weight:646.912
Hs Code.:

Synonyms:(2S,3R,5R,7S,8R)-3-Benzyloxy-2-benzyloxymethyl-8-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-5-methyl-7-(naphthalen-2-ylmethoxy)-oxocane

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Chemical Property of (2S,3R,5R,7S,8R)-3-Benzyloxy-2-benzyloxymethyl-8-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-5-methyl-7-(naphthalen-2-ylmethoxy)-oxocane

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Technology Process of (2S,3R,5R,7S,8R)-3-Benzyloxy-2-benzyloxymethyl-8-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-5-methyl-7-(naphthalen-2-ylmethoxy)-oxocane

There total 8 articles about (2S,3R,5R,7S,8R)-3-Benzyloxy-2-benzyloxymethyl-8-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-5-methyl-7-(naphthalen-2-ylmethoxy)-oxocane 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:

: Trifluoro-acetic acid (2R,3S,5S,7R,8S)-7-benzyloxy-8-benzyloxymethyl-5-methyl-3-(naphthalen-2-ylmethoxy)-oxocan-2-ylmethyl ester

: 33577-16-1
methyl methylsulfinylmethyl sulfide

: 871912-49-1
(2S,3R,5R,7S,8R)-3-Benzyloxy-2-benzyloxymethyl-8-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-5-methyl-7-(naphthalen-2-ylmethoxy)-oxocane

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; at -20 ℃; for 0.25h;
DOI:10.1016/j.tetlet.2005.09.164

Reference yield:

: (2R,4aR,6S,7R,9S,10aS)-6-Hydroxymethyl-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-7-ol

: 871912-49-1
(2S,3R,5R,7S,8R)-3-Benzyloxy-2-benzyloxymethyl-8-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-5-methyl-7-(naphthalen-2-ylmethoxy)-oxocane

Guidance literature:: Multi-step reaction with 6 steps

1: tBuOK; TBAI / tetrahydrofuran / 0.5 h / 23 °C

2: ethanedithiol; BF₃Et₂O / CH₂Cl₂ / 0.5 h / -20 °C

3: 93 percent / PPTS / benzene / 12 h / Heating

4: 85 percent / LiAlH₄; AlCl₃ / CH₂Cl₂; diethyl ether / 2 h / 23 °C

5: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

6: NHMDS / tetrahydrofuran / 0.25 h / -20 °C

With 2,6-dimethylpyridine; ethandithiol; lithium aluminium tetrahydride; aluminium trichloride; boron trifluoride diethyl etherate; potassium tert-butylate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1016/j.tetlet.2005.09.164

Reference yield:

: (2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-6-benzyloxymethyl-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocyclooctene

: 871912-49-1
(2S,3R,5R,7S,8R)-3-Benzyloxy-2-benzyloxymethyl-8-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-5-methyl-7-(naphthalen-2-ylmethoxy)-oxocane

Guidance literature:: Multi-step reaction with 5 steps

1: ethanedithiol; BF₃Et₂O / CH₂Cl₂ / 0.5 h / -20 °C

2: 93 percent / PPTS / benzene / 12 h / Heating

3: 85 percent / LiAlH₄; AlCl₃ / CH₂Cl₂; diethyl ether / 2 h / 23 °C

4: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

5: NHMDS / tetrahydrofuran / 0.25 h / -20 °C

With 2,6-dimethylpyridine; ethandithiol; lithium aluminium tetrahydride; aluminium trichloride; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1016/j.tetlet.2005.09.164