(2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-hydroxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-4-ol

Base Information

Chemical Name:(2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-hydroxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-4-ol
CAS No.:389119-51-1
Molecular Formula:C₂₅H₃₂O₆
Molecular Weight:428.525
Hs Code.:

Synonyms:(2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-hydroxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-4-ol

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Chemical Property of (2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-hydroxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-4-ol

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Technology Process of (2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-hydroxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-4-ol

There total 6 articles about (2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-hydroxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-4-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: 47.0%

: 4-pentenyl 2-O-benzyl-4,6-O-benzylidene-3-O-(4-methoxybenzyl)-β-D-galactopyranoside

: (2R,3R,4S,5R,6R)-5-Benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3,4-diol

: 389119-51-1
(2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-hydroxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-4-ol

Guidance literature:: 4-pentenyl 2-O-benzyl-4,6-O-benzylidene-3-O-(4-methoxybenzyl)-β-D-galactopyranoside; With lithium aluminium tetrahydride; In diethyl ether; dichloromethane; at 22 ℃; for 0.0833333h;

With aluminium trichloride; In diethyl ether; for 1h; Title compound not separated from byproducts; Heating;
DOI:10.1016/S0008-6215(01)00222-1

Reference yield:

: 100-39-0
benzyl bromide

: 389119-51-1
(2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-hydroxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 92 percent / 60 percent NaH / tetrahydrofuran / 24 °C

2.1: LiAlH₄ / CH₂Cl₂; diethyl ether / 0.08 h / 22 °C

2.2: 47 percent / AlCl₃ / diethyl ether / 1 h / Heating

With lithium aluminium tetrahydride; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0008-6215(01)00222-1

Reference yield:

: 100-52-7
benzaldehyde

: 389119-51-1
(2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-hydroxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 52 percent / formic acid / 1 h / 22 °C

2.1: Bu₂SnO / toluene / 0.83 h / Heating

2.2: 53 percent / tetrabutylammonium iodide / toluene / 90 °C

3.1: 92 percent / 60 percent NaH / tetrahydrofuran / 24 °C

4.1: LiAlH₄ / CH₂Cl₂; diethyl ether / 0.08 h / 22 °C

4.2: 47 percent / AlCl₃ / diethyl ether / 1 h / Heating

With lithium aluminium tetrahydride; formic acid; sodium hydride; di(n-butyl)tin oxide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1016/S0008-6215(01)00222-1