(2R,3S,4R)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran

Base Information

• Chemical Name: (2R,3S,4R)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran
• CAS No.: 111902-04-6
• Molecular Formula: C₂₅H₄₄O₄Si₂
• Molecular Weight: 464.793

Synonyms:(2R,3S,4R)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran

Chemical Property of (2R,3S,4R)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3S,4R)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran

There total 4 articles about (2R,3S,4R)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-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:

benzyl bromide (100-39-0) + 3,6-di-O-tert-butyldimethylsilyl-D-(-)-galactal (111902-03-5) → (2R,3S,4R)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran (111902-04-6)

Guidance literature:

With sodium hydride;

DOI:10.1016/S0040-4039(00)96025-8

Reference yield:

D-galactal (21193-75-9) → (2R,3S,4R)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran (111902-04-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.2 g / pyridine / CH₂Cl₂ / cooling

2: NaH / dimethylformamide / 3.5 h / 0 - 20 °C

With pyridine; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo034556r

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2R,3S,4R)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran (111902-04-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.2 g / pyridine / CH₂Cl₂ / cooling

2: NaH / dimethylformamide / 3.5 h / 0 - 20 °C

With pyridine; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo034556r

upstream raw materials:

benzyl bromide

3,6-di-O-tert-butyldimethylsilyl-D-(-)-galactal

t-butyldimethylsiyl triflate

D-galactal

Downstream raw materials:

4-O-benzyl-D-(-)-galactal

2,2-Dimethyl-propionic acid (2R,3R,4S,4aR,7R,8S,9aR)-3,4,8-tris-benzyloxy-2-benzyloxymethyl-5-oxo-3,4,4a,5,8,9a-hexahydro-2H,7H-1,6,9-trioxa-10-thia-anthracen-7-ylmethyl ester

2,2-Dimethyl-propionic acid (2R,3S,5R)-3-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylsulfanyl)-4,6-dioxo-tetrahydro-pyran-2-ylmethyl ester

4-O-benzyl-2-deoxy-6-O-pivaloyl-α,β-D-galactopyranose

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