[(2R,3R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol

Base Information

• Chemical Name: [(2R,3R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol
• CAS No.: 176242-24-3
• Molecular Formula: C₂₁H₃₆O₆Si
• Molecular Weight: 412.599

Synonyms:[(2R,3R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol

Chemical Property of [(2R,3R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol

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Technology Process of [(2R,3R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol

There total 1 articles about [(2R,3R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol 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:

p-Anisaldehyde dimethyl acetal (2186-92-7) + tert-butyldimethylsilyl chloride (18162-48-6) + D-glucal triacetate (2873-29-2) → [(2R,3R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol (176242-24-3)

Guidance literature:

With 1H-imidazole; Dowex 50X 8 H⁽¹⁺⁾; diisobutylaluminium hydride; Yield given. Multistep reaction; 2.) DMF; 3.) DMF; 4.) DCM, -10 deg C to 0 deg C;

DOI:10.1016/0040-4039(96)00046-9

Reference yield: 90.0%

[(2R,3R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol (176242-24-3) → (2S,3R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 ℃;

DOI:10.1016/0040-4039(96)00046-9

Reference yield: 84.0%

Methyltriphenylphosphonium bromide (1779-49-3) + [(2R,3R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol (176242-24-3) → tert-Butyl-[(2R,3R,4R,6S)-6-methoxy-3-(4-methoxy-benzyloxy)-2-vinyl-tetrahydro-pyran-4-yloxy]-dimethyl-silane (176242-25-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; -40 deg C then r.t., 12 h;

DOI:10.1016/0040-4039(96)00046-9

upstream raw materials:

p-Anisaldehyde dimethyl acetal

tert-butyldimethylsilyl chloride

D-glucal triacetate

Downstream raw materials:

tert-Butyl-[(2R,3R,4R,6S)-6-methoxy-3-(4-methoxy-benzyloxy)-2-vinyl-tetrahydro-pyran-4-yloxy]-dimethyl-silane

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