(2R,3S,5R,6S)-2-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-5-triisopropylsilanyloxy-6-vinyl-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2R,3S,5R,6S)-2-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-5-triisopropylsilanyloxy-6-vinyl-tetrahydro-pyran-3-ol
• CAS No.: 370886-66-1
• Molecular Formula: C₃₇H₅₀O₅Si
• Molecular Weight: 602.886

Synonyms:(2R,3S,5R,6S)-2-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-5-triisopropylsilanyloxy-6-vinyl-tetrahydro-pyran-3-ol

Chemical Property of (2R,3S,5R,6S)-2-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-5-triisopropylsilanyloxy-6-vinyl-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3S,5R,6S)-2-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-5-triisopropylsilanyloxy-6-vinyl-tetrahydro-pyran-3-ol

There total 4 articles about (2R,3S,5R,6S)-2-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-5-triisopropylsilanyloxy-6-vinyl-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: 100.0%

mono-4-methoxytrityl chloride (14470-28-1) + (2R,3S,5R,6S)-2-Hydroxymethyl-5-triisopropylsilanyloxy-6-vinyl-tetrahydro-pyran-3-ol (370886-82-1) → (2R,3S,5R,6S)-2-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-5-triisopropylsilanyloxy-6-vinyl-tetrahydro-pyran-3-ol (370886-66-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(01)01067-X

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (2R,3S,5R,6S)-2-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-5-triisopropylsilanyloxy-6-vinyl-tetrahydro-pyran-3-ol (370886-66-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2: CSA / methanol; CH₂Cl₂ / 20 °C

3: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

With 2,6-dimethylpyridine; dmap; camphor-10-sulfonic acid; triethylamine; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(01)01067-X

Reference yield:

(2R,4aR,6S,7R)-2-Phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol → (2R,3S,5R,6S)-2-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-5-triisopropylsilanyloxy-6-vinyl-tetrahydro-pyran-3-ol (370886-66-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2: CSA / methanol; CH₂Cl₂ / 20 °C

3: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

With 2,6-dimethylpyridine; dmap; camphor-10-sulfonic acid; triethylamine; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(01)01067-X

upstream raw materials:

mono-4-methoxytrityl chloride

(2R,3S,5R,6S)-2-Hydroxymethyl-5-triisopropylsilanyloxy-6-vinyl-tetrahydro-pyran-3-ol

triisopropylsilyl trifluoromethanesulfonate

Downstream raw materials:

(2R,4R,4aS,6R,7R,8aR)-7-Benzyloxy-2-{3-[(2R,3R,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-prop-1-ynyl}-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-ol

((2R,3R,4S)-4-Benzyloxy-2-{3-[(2R,4R,4aS,6R,7R,8aR)-7-benzyloxy-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-yl]-prop-2-ynyl}-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

1-((2R,4S,4aR,6R,7R,8aR)-7-Benzyloxy-6-benzyloxymethyl-4-chloro-octahydro-pyrano[3,2-b]pyran-2-yl)-3-[(2R,3S,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propane-1,2-diol

1-((2R,4S,4aR,6R,7R,8aR)-7-Benzyloxy-6-benzyloxymethyl-4-chloro-octahydro-pyrano[3,2-b]pyran-2-yl)-3-[(2R,3S,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propane-1,2-dione

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