Benzoic acid (1R,2R,3R)-3-[(2S,3R,4S,5R,6R)-4,5-bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-pent-4-ynyl ester

Base Information

• Chemical Name: Benzoic acid (1R,2R,3R)-3-[(2S,3R,4S,5R,6R)-4,5-bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-pent-4-ynyl ester
• CAS No.: 330189-36-1
• Molecular Formula: C₆₇H₇₇IO₇Si₃
• Molecular Weight: 1205.51

Synonyms:Benzoic acid (1R,2R,3R)-3-[(2S,3R,4S,5R,6R)-4,5-bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-pent-4-ynyl ester

Chemical Property of Benzoic acid (1R,2R,3R)-3-[(2S,3R,4S,5R,6R)-4,5-bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-pent-4-ynyl ester

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Technology Process of Benzoic acid (1R,2R,3R)-3-[(2S,3R,4S,5R,6R)-4,5-bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-pent-4-ynyl ester

There total 3 articles about Benzoic acid (1R,2R,3R)-3-[(2S,3R,4S,5R,6R)-4,5-bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-pent-4-ynyl ester 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: 83.0%

tert-butylchlorodiphenylsilane (58479-61-1) + Benzoic acid (1R,2R,3R)-3-[(2S,3R,4S,5R,6R)-4,5-bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-2-hydroxy-1-methyl-pent-4-ynyl ester (330189-27-0) → Benzoic acid (1R,2R,3R)-3-[(2S,3R,4S,5R,6R)-4,5-bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-pent-4-ynyl ester (330189-36-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 48h;

DOI:10.1016/S0022-328X(00)00643-4

Reference yield:

(2R,3R,4R)-hex-5-yn-2,3,4-triol 2-benzoate ester (279684-69-4) → Benzoic acid (1R,2R,3R)-3-[(2S,3R,4S,5R,6R)-4,5-bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-pent-4-ynyl ester (330189-36-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / TBSOTf / CH₂Cl₂ / 0.33 h / -75 °C

2: 83 percent / imidazole / dimethylformamide / 48 h

With 1H-imidazole; t-butyldimethylsiyl triflate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0022-328X(00)00643-4

Reference yield:

Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yl ester → Benzoic acid (1R,2R,3R)-3-[(2S,3R,4S,5R,6R)-4,5-bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-pent-4-ynyl ester (330189-36-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / TBSOTf / CH₂Cl₂ / 0.33 h / -75 °C

2: 83 percent / imidazole / dimethylformamide / 48 h

With 1H-imidazole; t-butyldimethylsiyl triflate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0022-328X(00)00643-4

upstream raw materials:

tert-butylchlorodiphenylsilane

Benzoic acid (1R,2R,3R)-3-[(2S,3R,4S,5R,6R)-4,5-bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-2-hydroxy-1-methyl-pent-4-ynyl ester

(2R,3R,4R)-hex-5-yn-2,3,4-triol 2-benzoate ester

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