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

Base Information

• Chemical Name: (2S,3S,4R,5S,6S)-2-Benzyloxy-5-[(2S,3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-4,6-dimethyl-3-phenylsulfanyl-tetrahydro-pyran-4-ol
• CAS No.: 400738-29-6
• Molecular Formula: C₃₉H₅₄O₇S₂Si
• Molecular Weight: 727.071

Synonyms:(2S,3S,4R,5S,6S)-2-Benzyloxy-5-[(2S,3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-4,6-dimethyl-3-phenylsulfanyl-tetrahydro-pyran-4-ol

Chemical Property of (2S,3S,4R,5S,6S)-2-Benzyloxy-5-[(2S,3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-4,6-dimethyl-3-phenylsulfanyl-tetrahydro-pyran-4-ol

Chemical Property:

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Technology Process of (2S,3S,4R,5S,6S)-2-Benzyloxy-5-[(2S,3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-4,6-dimethyl-3-phenylsulfanyl-tetrahydro-pyran-4-ol

There total 18 articles about (2S,3S,4R,5S,6S)-2-Benzyloxy-5-[(2S,3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-4,6-dimethyl-3-phenylsulfanyl-tetrahydro-pyran-4-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: 45.0%

tert-Butyl-((2R,3R,4S,5R)-6-fluoro-4-methoxy-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane + (2S,3S,4R,5S,6S)-6-Benzyloxy-2,4-dimethyl-5-phenylsulfanyl-tetrahydro-pyran-3,4-diol (400738-14-9) → (2S,3S,4R,5S,6S)-6-Benzyloxy-4-[(3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-2,4-dimethyl-5-phenylsulfanyl-tetrahydro-pyran-3-ol + (2S,3S,4R,5S,6S)-2-Benzyloxy-5-[(2S,3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-4,6-dimethyl-3-phenylsulfanyl-tetrahydro-pyran-4-ol (400738-29-6)

Guidance literature:

With tin(ll) chloride; In diethyl ether; at 0 - 25 ℃; for 12h;

DOI:10.1002/1521-3773(20011015)40:20<3849::AID-ANIE3849>3.0.CO;2-M

Reference yield: 45.0%

tert-Butyl-((2R,3R,4S,5R)-6-fluoro-4-methoxy-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane + (2S,3S,4R,5S,6S)-6-Benzyloxy-2,4-dimethyl-5-phenylsulfanyl-tetrahydro-pyran-3,4-diol (400738-14-9) → (2S,3S,4R,5S,6S)-2-Benzyloxy-5-[(2S,3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-4,6-dimethyl-3-phenylsulfanyl-tetrahydro-pyran-4-ol (400738-29-6) + (2S,3S,4R,5S,6S)-6-Benzyloxy-4-[(2S,3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-2,4-dimethyl-5-phenylsulfanyl-tetrahydro-pyran-3-ol

Guidance literature:

With 4 A molecular sieve; tin(ll) chloride; In diethyl ether; at 25 ℃; for 12h;

DOI:10.1021/ja0304953

Reference yield:

(2R,3S,4R,5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3,4-diol (214483-40-6) → (2S,3S,4R,5S,6S)-2-Benzyloxy-5-[(2S,3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-4,6-dimethyl-3-phenylsulfanyl-tetrahydro-pyran-4-ol (400738-29-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: nBu₂SnO / toluene / 6 h / Heating

1.2: 83 percent / cesium fluoride / dimethylformamide / 1 h / 55 °C

2.1: dimethylaminosulfur trifluoride / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 45 percent / 4A molecular sieves; SnCl₂ / diethyl ether / 12 h / 25 °C

With dimethylaminosulphur trifluoride; 4 A molecular sieve; di(n-butyl)tin oxide; tin(ll) chloride; In diethyl ether; dichloromethane; toluene;

DOI:10.1021/ja0304953

upstream raw materials:

(2S,3S,4R,5S,6S)-6-Benzyloxy-2,4-dimethyl-5-phenylsulfanyl-tetrahydro-pyran-3,4-diol

(2R,3S,4R,5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3,4-diol

benzyl alcohol

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

Downstream raw materials:

(2S,3S,4R,5S,6S)-2-Benzyloxy-5-[(2S,3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-4,6-dimethyl-3-phenylsulfanyl-4-triethylsilanyloxy-tetrahydro-pyran

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