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

Base Information

Chemical Name:(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-oxiranyl-tetrahydro-pyran-3-ol
CAS No.:77737-60-1
Molecular Formula:C₂₉H₃₂O₆
Molecular Weight:476.569
Hs Code.:

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

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

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

There total 4 articles about (2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-oxiranyl-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: 75.0%

: 77737-59-8
(2β,3S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-vinyltetrahydro-2H-pyran-3-ol

: 77737-60-1
(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-oxiranyl-tetrahydro-pyran-3-ol

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 25 ℃; for 18h;
DOI:10.1016/S0008-6215(00)84618-2

Reference yield:

: 81969-44-0
1,2-di-O-acetyl-3,4,6-tri-O-benzyl-D-galactopyranose

: 77737-60-1
(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-oxiranyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: saturated hydrogen bromide / acetic acid; CH₂Cl₂ / 0.5 h / 0 °C

2: 85 percent / tetrahydrofuran / -78 deg C; 1 h, 0 deg C

3: 75 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 18 h / 25 °C

With hydrogen bromide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; acetic acid;
DOI:10.1016/S0008-6215(00)84618-2

Reference yield:

: 77790-47-7
2-O-acetyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl bromide

: 77737-60-1
(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-oxiranyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / tetrahydrofuran / -78 deg C; 1 h, 0 deg C

2: 75 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 18 h / 25 °C

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0008-6215(00)84618-2