(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-ol
CAS No.:439264-95-6
Molecular Formula:C₂₃H₃₀O₅
Molecular Weight:386.488
Hs Code.:

Synonyms:(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-ol

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Chemical Property of (2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-ol

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Technology Process of (2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-ol

There total 2 articles about (2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-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: 48.0%

: 439264-93-4
3-((5S,6R)-5-Benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-propionic acid methyl ester

: (2R,3S,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-ol

: 439264-95-6
(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-ol

Guidance literature:: 3-((5S,6R)-5-Benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-propionic acid methyl ester; With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃;

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; Further stages.;
DOI:10.1021/jo025566f

Reference yield:

: 177328-07-3
Trifluoro-methanesulfonic acid (5S,6R)-5-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl ester

: 439264-95-6
(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: Zn-Cu couple / benzene; N,N-dimethyl-acetamide / 2 h / Heating

1.2: 78 percent / Pd(PPh₃)4 / benzene; N,N-dimethyl-acetamide / 20 °C

2.1: BH₃*SMe₂ / tetrahydrofuran / 0 - 20 °C

2.2: 48 percent / 1N NaOH; 30percent H₂O₂ / tetrahydrofuran / 20 °C

With dimethylsulfide borane complex; copper; zinc; In tetrahydrofuran; N,N-dimethyl acetamide; benzene;
DOI:10.1021/jo025566f

Reference yield: 94.0%

: 439264-95-6
(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-ol

: 291304-35-3
(4aS,6R,7S,8aR)-7-Benzyloxy-6-benzyloxymethyl-hexahydro-pyrano[3,2-b]pyran-2-one

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium bromide; In dichloromethane; water; at 0 ℃;
DOI:10.1021/jo025566f