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

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Chemical Name:2-[(2S,3S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-ethanol
CAS No.:273918-25-5
Molecular Formula:C₂₇H₄₀O₆SeSi
Molecular Weight:567.657
Hs Code.:

Synonyms:2-[(2S,3S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-ethanol

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Chemical Property of 2-[(2S,3S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-ethanol

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Technology Process of 2-[(2S,3S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-ethanol

There total 7 articles about 2-[(2S,3S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-ethanol 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: 95.0%

: 306937-32-6
Benzoic acid 2-[(2S,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-ethyl ester

: 273918-25-5
2-[(2S,3S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-ethanol

Guidance literature:: With sodium methylate; In methanol; at 25 ℃; for 3h;
DOI:10.1002/(SICI)1521-3773(20000317)39:6<1089::AID-ANIE1089>3.0.CO;2-V

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 273918-25-5
2-[(2S,3S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-ethanol

Guidance literature:: Multi-step reaction with 4 steps

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

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

3: 94 percent / SnCl₂; molecular sieves 4 Angstroem / diethyl ether / 3 h / 0 - 25 °C

4: 95 percent / NaOMe; MeOH / 3 h / 25 °C

With 2,6-dimethylpyridine; methanol; 4 A molecular sieve; sodium methylate; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride; In diethyl ether; dichloromethane; 1: Etherification / 2: Rearrangement / 3: Glycosidation / 4: Debenzoylation;
DOI:10.1002/1521-3765(20000901)6:17<3166::AID-CHEM3166>3.0.CO;2-Z

Reference yield:

: 256342-00-4
(2S,3R,4R,5R)-5-(4-Methoxy-benzyloxy)-2-phenylselanyl-tetrahydro-pyran-3,4-diol

: 273918-25-5
2-[(2S,3S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-ethanol

Guidance literature:: Multi-step reaction with 4 steps

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

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

3: 94 percent / SnCl₂; molecular sieves 4 Angstroem / diethyl ether / 3 h / 0 - 25 °C

4: 95 percent / NaOMe; MeOH / 3 h / 25 °C

With 2,6-dimethylpyridine; methanol; 4 A molecular sieve; sodium methylate; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride; In diethyl ether; dichloromethane; 1: Etherification / 2: Rearrangement / 3: Glycosidation / 4: Debenzoylation;
DOI:10.1002/1521-3765(20000901)6:17<3166::AID-CHEM3166>3.0.CO;2-Z