(2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-butenyl)-tetrahydro-pyran-3-acetate

Base Information

Chemical Name:(2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-butenyl)-tetrahydro-pyran-3-acetate
CAS No.:440362-87-8
Molecular Formula:C₃₃H₃₈O₆
Molecular Weight:530.661
Hs Code.:

Synonyms:(2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-butenyl)-tetrahydro-pyran-3-acetate

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Chemical Property of (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-butenyl)-tetrahydro-pyran-3-acetate

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Technology Process of (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-butenyl)-tetrahydro-pyran-3-acetate

There total 3 articles about (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-butenyl)-tetrahydro-pyran-3-acetate 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: 79.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 440362-97-0
Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-oxo-propyl)-tetrahydro-pyran-3-yl ester

: 440362-87-8
(2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-butenyl)-tetrahydro-pyran-3-acetate

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at 0 - 20 ℃;

Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-oxo-propyl)-tetrahydro-pyran-3-yl ester; In tetrahydrofuran; at 0 ℃; for 0.25h;
DOI:10.1016/S0040-4020(02)00057-1

Reference yield:

: 193546-84-8
3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene

: 440362-87-8
(2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-butenyl)-tetrahydro-pyran-3-acetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: BH₃ / tetrahydrofuran / 2 h / 0 °C

1.2: 73 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

2.1: (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -60 °C

2.2: 94 percent / NEt₃ / CH₂Cl₂ / -60 - 20 °C

3.1: BuLi / tetrahydrofuran / 0 - 20 °C

3.2: 79 percent / tetrahydrofuran / 0.25 h / 0 °C

With n-butyllithium; oxalyl dichloride; borane; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(02)00057-1

Reference yield:

: 440362-96-9
Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester

: 440362-87-8
(2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-butenyl)-tetrahydro-pyran-3-acetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -60 °C

1.2: 94 percent / NEt₃ / CH₂Cl₂ / -60 - 20 °C

2.1: BuLi / tetrahydrofuran / 0 - 20 °C

2.2: 79 percent / tetrahydrofuran / 0.25 h / 0 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(02)00057-1