(2S,3S,4S,5R)-2-(2-Hydroxy-ethoxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-ol

Base Information

Chemical Name:(2S,3S,4S,5R)-2-(2-Hydroxy-ethoxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-ol
CAS No.:273918-26-6
Molecular Formula:C₂₁H₂₆O₆Se
Molecular Weight:453.394
Hs Code.:

Synonyms:(2S,3S,4S,5R)-2-(2-Hydroxy-ethoxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-ol

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Chemical Property of (2S,3S,4S,5R)-2-(2-Hydroxy-ethoxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-ol

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Technology Process of (2S,3S,4S,5R)-2-(2-Hydroxy-ethoxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-ol

There total 7 articles about (2S,3S,4S,5R)-2-(2-Hydroxy-ethoxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-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: 95.0%

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

: 273918-26-6
(2S,3S,4S,5R)-2-(2-Hydroxy-ethoxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 1h;
DOI:10.1002/(SICI)1521-3773(20000317)39:6<1089::AID-ANIE1089>3.0.CO;2-V

Reference yield:

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

: 273918-26-6
(2S,3S,4S,5R)-2-(2-Hydroxy-ethoxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 5 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

5: 95 percent / TBAF / tetrahydrofuran / 1 h / 25 °C

With 2,6-dimethylpyridine; methanol; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Etherification / 2: Rearrangement / 3: Glycosidation / 4: Debenzoylation / 5: Silyl ether cleavage;
DOI:10.1002/1521-3765(20000901)6:17<3166::AID-CHEM3166>3.0.CO;2-Z

Reference yield:

: 256341-86-3
tert-Butyl-[(3S,4S,5R)-2-fluoro-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yloxy]-dimethyl-silane

: 273918-26-6
(2S,3S,4S,5R)-2-(2-Hydroxy-ethoxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / SnCl₂; molecular sieves 4 Angstroem / diethyl ether / 3 h / 0 - 25 °C

2: 95 percent / NaOMe; MeOH / 3 h / 25 °C

3: 95 percent / TBAF / tetrahydrofuran / 1 h / 25 °C

With methanol; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; tin(ll) chloride; In tetrahydrofuran; diethyl ether; 1: Glycosidation / 2: Debenzoylation / 3: Silyl ether cleavage;
DOI:10.1002/1521-3765(20000901)6:17<3166::AID-CHEM3166>3.0.CO;2-Z