(3R,4S,5S,6S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (3R,4S,5S,6S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-3-ol
• CAS No.: 206124-74-5
• Molecular Formula: C₁₉H₃₂O₄Si
• Molecular Weight: 352.546
• Mol file: 206124-74-5.mol

Synonyms:(3R,4S,5S,6S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-3-ol

Chemical Property of (3R,4S,5S,6S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

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MSDS Files:

Useful:

Technology Process of (3R,4S,5S,6S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-3-ol

There total 1 articles about (3R,4S,5S,6S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-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: 55.0%

benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-α-D-arabinopyranoside (115983-66-9) → (3R,4S,5S,6S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-3-ol (206124-74-5)

Guidance literature:

With 1H-imidazole; sodium hydride; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(98)00120-3

Reference yield: 74.0%

trimethylaluminum (75-24-1) + (3R,4S,5S,6S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-3-ol (206124-74-5) → (2R,3S,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexane-1,2-diol

Guidance literature:

In hexane; at 69 ℃; for 10h;

DOI:10.1016/S0040-4020(98)00120-3

Reference yield:

(3R,4S,5S,6S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-3-ol (206124-74-5) → (2R,3S,4S)-5-Benzyloxy-4-methyl-hexane-1,2,3-triol

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / hexane / 10 h / 69 °C

2: TBAF / tetrahydrofuran / 4 h / Ambient temperature

With tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane;

DOI:10.1016/S0040-4020(98)00120-3

upstream raw materials:

benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-α-D-arabinopyranoside