(2R,3R,6S)-6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-2H-pyran-3-ol

Base Information

• Chemical Name: (2R,3R,6S)-6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-2H-pyran-3-ol
• CAS No.: 247145-67-1
• Molecular Formula: C₁₉H₃₀O₄Si
• Molecular Weight: 350.53

Synonyms:(2R,3R,6S)-6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-2H-pyran-3-ol

Chemical Property of (2R,3R,6S)-6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-2H-pyran-3-ol

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Technology Process of (2R,3R,6S)-6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-2H-pyran-3-ol

There total 2 articles about (2R,3R,6S)-6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-2H-pyran-3-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:

benzoic acid 6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yl ester → (2R,3R,6S)-6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-2H-pyran-3-ol (247145-67-1)

Guidance literature:

With sodium methylate; In methanol; for 3h;

DOI:10.1021/jo026161y

Reference yield:

(2R,3S,6S)-6-(benzyloxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol (81389-87-9) → (2R,3R,6S)-6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-2H-pyran-3-ol (247145-67-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / PPh₃; DEAD / tetrahydrofuran / 20 °C

2: 0.37 g / MeONa / methanol / 3 h

With sodium methylate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; 1: Mitsunobu reaction;

DOI:10.1021/jo026161y

Reference yield:

(2R,3R,6S)-6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-2H-pyran-3-ol (247145-67-1) → (2S,5R,6R)-2-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3,4,5-triol

Guidance literature:

With osmium(VIII) oxide; N,N,N,N,-tetramethylethylenediamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/jo026161y

upstream raw materials:

(2R,3S,6S)-6-(benzyloxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol

Downstream raw materials:

(2S,3S,6S)-6-(tert-butyldimethylsilyloxymethyl)-3-(2,2,2-trichloroacetylamino)-2-(benzyloxy)-2H-3,6-dihydropyran

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