(2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-ethynyl-2-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran

Base Information

Chemical Name:(2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-ethynyl-2-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran
CAS No.:273926-03-7
Molecular Formula:C₃₀H₃₂O₆
Molecular Weight:488.58
Hs Code.:

Synonyms:(2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-ethynyl-2-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran

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Chemical Property of (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-ethynyl-2-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran

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Technology Process of (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-ethynyl-2-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran

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

: 558-13-4
carbon tetrabromide

: 130523-98-7
(2S,3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde

: 273926-03-7
(2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-ethynyl-2-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran

Guidance literature:: carbon tetrabromide; (2S,3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde; With triphenylphosphine; In dichloromethane;

With tert.-butyl lithium; In tetrahydrofuran; at -50 ℃; Further stages.;
DOI:10.1021/ol0000408

Reference yield:

: 90633-95-7,94827-31-3,90633-90-2
methyl 2,3-bis-O-benzyl-4-O-[(4-methoxyphenyl)methyl]-α-D-glucopyranoside

: 273926-03-7
(2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-ethynyl-2-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 2 steps

1.1: Dess-Martine periodinane / CH₂Cl₂

2.1: PPh₃ / CH₂Cl₂

2.2: t-BuLi / tetrahydrofuran / -50 °C

With Dess-Martin periodane; triphenylphosphine; In dichloromethane; 1.1: Dess-Martin oxidation / 2.1: Condensation / 2.2: Elimination;
DOI:10.1021/ol0000408