(2R,3S,4R,5S,6S)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3S,4R,5S,6S)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran
• CAS No.: 1007224-13-6
• Molecular Formula: C₂₅H₄₆O₄SSi₂
• Molecular Weight: 498.875

Synonyms:(2R,3S,4R,5S,6S)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran

Chemical Property of (2R,3S,4R,5S,6S)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran

Chemical Property:

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Technology Process of (2R,3S,4R,5S,6S)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran

There total 2 articles about (2R,3S,4R,5S,6S)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran 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: 99.0%

(2R,3S,4S,5S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol (1007224-17-0) + t-butyldimethylsiyl triflate (69739-34-0) → (2R,3S,4R,5S,6S)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran (1007224-13-6)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/jo702250z

Reference yield:

phenylthiotrimethylsilane (4551-15-9) + C19H42O5Si2 (1118588-72-9) → (2R,3S,4R,5S,6S)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran (1007224-13-6) + (2S,3S,4R,5S,6S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran (400737-73-7)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; zinc(II) iodide; In dichloromethane; at 20 ℃; for 2h; optical yield given as %de;

DOI:10.1021/ol802829n

Reference yield: 92.0%

(3S,4R)-1-(tert-butyl-dimethyl-silanyl)-5-(4-methoxy-benzyloxy)-4-methyl-pent-1-yn-3-ol (1007224-14-7) + (2R,3S,4R,5S,6S)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran (1007224-13-6) → (2R,3S,4R,5S,6S)-2-{(S)-3-(tert-butyl-dimethyl-silanyl)-1-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-prop-2-ynyloxy}-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-tetrahydro-pyran (1007224-18-1) + (2S,3S,4R,5S,6S)-2-{(S)-3-(tert-butyl-dimethyl-silanyl)-1-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-prop-2-ynyloxy}-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-tetrahydro-pyran

Guidance literature:

With N-iodo-succinimide; 4 A molecular sieve; In toluene; at -30 ℃; for 1h;

DOI:10.1021/jo702250z

upstream raw materials:

(2R,3S,4S,5S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

t-butyldimethylsiyl triflate

phenylthiotrimethylsilane

C₁₉H₄₂O₅Si₂

Downstream raw materials:

(2R,3S,4R,5S,6S)-2-{(S)-3-(tert-butyl-dimethyl-silanyl)-1-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-prop-2-ynyloxy}-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-tetrahydro-pyran

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