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

Base Information

Chemical Name:Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-oxo-propyl)-tetrahydro-pyran-3-yl ester
CAS No.:440362-97-0
Molecular Formula:C₃₂H₃₆O₇
Molecular Weight:532.634
Hs Code.:

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

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Chemical Property of Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-oxo-propyl)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-oxo-propyl)-tetrahydro-pyran-3-yl ester

There total 2 articles about Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-oxo-propyl)-tetrahydro-pyran-3-yl ester 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: 94.0%

: 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

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

Guidance literature:: Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -60 ℃; for 0.5h;

With triethylamine; In dichloromethane; at -60 - 20 ℃;
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

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

Guidance literature:: Multi-step reaction with 2 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

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

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