(4S,5R,6R)-5,6-Bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (4S,5R,6R)-5,6-Bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl ester
• CAS No.: 213906-26-4
• Molecular Formula: C₃₃H₄₀O₆Si
• Molecular Weight: 560.763

Synonyms:(4S,5R,6R)-5,6-Bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl ester

Chemical Property of (4S,5R,6R)-5,6-Bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (4S,5R,6R)-5,6-Bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl ester

There total 1 articles about (4S,5R,6R)-5,6-Bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl 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:

benzyl chloride (100-44-7) + (4S,5R,6R)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-5,6-dihydro-4H-pyran-2-carboxylic acid → (4S,5R,6R)-4,5,6-Tris-benzyloxy-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl ester (188003-26-1) + (4S,5R,6R)-5,6-Bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl ester (213906-26-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 48h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0008-6215(98)00118-9

Reference yield: 75.0%

N-(4-methoxybenzyl)-2,2,2-trichloroacetamide (123558-64-5) + (4S,5R,6R)-5,6-Bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl ester (213906-26-4) → (4S,5R,6R)-5,6-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl ester

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 20h; Ambient temperature;

DOI:10.1016/S0008-6215(98)00118-9

Reference yield:

(4S,5R,6R)-5,6-Bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl ester (213906-26-4) → (4S,5R,6R)-5,6-Bis-benzyloxy-4-hydroxy-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / 24 h / Ambient temperature

2: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

With tetrabutyl ammonium fluoride; sodium methylate; In tetrahydrofuran;

DOI:10.1016/S0008-6215(98)00118-9

upstream raw materials:

benzyl chloride

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