(2R,3S,6S)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol

Base Information

• Chemical Name: (2R,3S,6S)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol
• CAS No.: 81389-86-8
• Molecular Formula: C₁₃H₁₆O₄
• Molecular Weight: 236.268
• Mol file: 81389-86-8.mol

Synonyms:(2R,3S,6S)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol

Chemical Property of (2R,3S,6S)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,6S)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol

There total 11 articles about (2R,3S,6S)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-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: 98.0%

benzyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enpyranoside (81389-84-6) → (2R,3S,6S)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol (81389-86-8)

Guidance literature:

With methanol; sodium methylate;

DOI:10.1016/j.tet.2009.07.088

Reference yield: 70.0%

benzyl 4,6-di-O-acetyl-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside (69247-18-3,81389-84-6,81389-85-7) → (2R,3S,6S)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol (81389-86-8)

Guidance literature:

With water; triethylamine; In methanol; for 4h; Ambient temperature;

DOI:10.1021/jo00132a037

Reference yield:

D-glucal triacetate (2873-29-2) → (2R,3S,6S)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol (81389-86-8)

Guidance literature:

Multi-step reaction with 2 steps

1: BF₃*Et₂O / benzene / 0.5 h / Ambient temperature

2: Amberlite IRA-400 / methanol / 24 h / Ambient temperature

With Amberlite IRA-400; boron trifluoride diethyl etherate; In methanol; benzene;

DOI:10.1246/cl.1994.1083

upstream raw materials:

benzyl 4,6-di-O-acetyl-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside

benzyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enpyranoside

benzyl alcohol

D-glucal triacetate

Downstream raw materials:

(2R,3S,6S)-6-(benzyloxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol

Methanesulfonic acid (2R,3S,6S)-6-benzyloxy-2-methanesulfonyloxymethyl-3,6-dihydro-2H-pyran-3-yl ester

benzyl 6-O-benzoyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

benzyl 2,3,4-trideoxy-α-D-glycero-hex-2-enopyranoside