(3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol
• CAS No.: 354114-14-0
• Molecular Formula: C₃₃H₃₄O₅S
• Molecular Weight: 542.696

Synonyms:(3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

Chemical Property of (3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

Chemical Property:

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Technology Process of (3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

There total 2 articles about (3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol 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:

Acetic acid (3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester → (3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol (354114-14-0)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1h;

DOI:10.1002/1521-3765(20001002)6:19<3608::AID-CHEM3608>3.0.CO;2-Q

Reference yield:

thiophenol (108-98-5) → (3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol (354114-14-0)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C / Inert atmosphere

2: sodium methylate / methanol / 18 h / pH 10 / Inert atmosphere

With boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane;

DOI:10.1039/c7ob02968c

Reference yield: 100.0%

(3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol (354114-14-0) + Chloro-dimethyl-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane (138181-78-9) → ((3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane (138181-79-0,138256-55-0)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; for 0.166667h; Ambient temperature;

DOI:10.1021/ja00029a047

upstream raw materials:

thiophenol

Downstream raw materials:

((3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-methoxy-dimethyl-silane

((3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane

((3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane

2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

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