Acetic acid (2S,3R,4S,5R,6R)-3-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6R)-3-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-4-yl ester
• CAS No.: 306937-44-0
• Molecular Formula: C₃₆H₅₄O₁₁SeSi
• Molecular Weight: 769.864

Synonyms:Acetic acid (2S,3R,4S,5R,6R)-3-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-3-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-4-yl ester

Chemical Property:

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Technology Process of Acetic acid (2S,3R,4S,5R,6R)-3-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-4-yl ester

There total 6 articles about Acetic acid (2S,3R,4S,5R,6R)-3-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-4-yl 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: 66.0%

tert-Butyl-[(3S,4S,5R)-2-fluoro-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yloxy]-dimethyl-silane (256341-86-3) + Acetic acid (2S,3R,4R,5R,6R)-3-hydroxy-2,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-4-yl ester → Acetic acid (2S,3R,4S,5R,6R)-3-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-4-yl ester (306937-44-0)

Guidance literature:

With tin(ll) chloride; In dichloromethane;

DOI:10.1002/(SICI)1521-3773(20000317)39:6<1089::AID-ANIE1089>3.0.CO;2-V

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → Acetic acid (2S,3R,4S,5R,6R)-3-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-4-yl ester (306937-44-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

2: 100 percent / DAST / CH₂Cl₂ / 0.5 h / 0 °C

3: 66 percent / SnCl₂; molecular sieves 4 Angstroem / diethyl ether / 3 h / 0 °C

With 2,6-dimethylpyridine; 4 A molecular sieve; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride; In diethyl ether; dichloromethane; 1: Etherification / 2: Rearrangement / 3: Glycosidation;

DOI:10.1002/1521-3765(20000901)6:17<3166::AID-CHEM3166>3.0.CO;2-Z

Reference yield:

(2S,3R,4R,5R)-5-(4-Methoxy-benzyloxy)-2-phenylselanyl-tetrahydro-pyran-3,4-diol (256342-00-4) → Acetic acid (2S,3R,4S,5R,6R)-3-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-4-yl ester (306937-44-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

2: 100 percent / DAST / CH₂Cl₂ / 0.5 h / 0 °C

3: 66 percent / SnCl₂; molecular sieves 4 Angstroem / diethyl ether / 3 h / 0 °C

With 2,6-dimethylpyridine; 4 A molecular sieve; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride; In diethyl ether; dichloromethane; 1: Etherification / 2: Rearrangement / 3: Glycosidation;

DOI:10.1002/1521-3765(20000901)6:17<3166::AID-CHEM3166>3.0.CO;2-Z

upstream raw materials:

tert-Butyl-[(3S,4S,5R)-2-fluoro-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yloxy]-dimethyl-silane

t-butyldimethylsiyl triflate

(2S,3R,4R,5R)-5-(4-Methoxy-benzyloxy)-2-phenylselanyl-tetrahydro-pyran-3,4-diol

(2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-phenylselanyl-tetrahydro-pyran-3-ol

Downstream raw materials:

C₂₈H₄₆O₁₀Si

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