(3S,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-3-methyl-2-oxohexahydrofuro[2,3-b]pyran

Base Information

Chemical Name:(3S,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-3-methyl-2-oxohexahydrofuro[2,3-b]pyran
CAS No.:1203550-51-9
Molecular Formula:C₃₀H₃₂O₆
Molecular Weight:488.58
Hs Code.:

Synonyms:(3S,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-3-methyl-2-oxohexahydrofuro[2,3-b]pyran

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Chemical Property of (3S,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-3-methyl-2-oxohexahydrofuro[2,3-b]pyran

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Technology Process of (3S,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-3-methyl-2-oxohexahydrofuro[2,3-b]pyran

There total 2 articles about (3S,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-3-methyl-2-oxohexahydrofuro[2,3-b]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: 90.0%

: 1124225-72-4
(3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran

: 74-88-4
methyl iodide

: 1203550-51-9
(3S,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-3-methyl-2-oxohexahydrofuro[2,3-b]pyran

Guidance literature:: (3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.75h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at -78 ℃; optical yield given as %de; stereoselective reaction; Inert atmosphere;
DOI:10.1039/b918893m

Reference yield:

: 946512-97-6
methyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-[(bis-methoxycarbonyl)methyl]-β-D-glucopyranoside

: 1203550-51-9
(3S,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-3-methyl-2-oxohexahydrofuro[2,3-b]pyran

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium hydroxide monohydrate / methanol; water / 1 h / Inert atmosphere; Reflux

2.1: acetic acid / toluene / 1 h / 110 °C / pH 3 - 4 / Inert atmosphere

3.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

With lithium hydroxide monohydrate; potassium hexamethylsilazane; acetic acid; In tetrahydrofuran; methanol; water; toluene;
DOI:10.1016/j.tet.2011.01.069