Acetic acid (2S,3R,4S,5R)-3-acetoxy-5-(4-methoxy-benzyloxy)-2-phenylselanyl-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Acetic acid (2S,3R,4S,5R)-3-acetoxy-5-(4-methoxy-benzyloxy)-2-phenylselanyl-tetrahydro-pyran-4-yl ester
CAS No.:273918-24-4
Molecular Formula:C₂₃H₂₆O₇Se
Molecular Weight:493.415
Hs Code.:

Synonyms:Acetic acid (2S,3R,4S,5R)-3-acetoxy-5-(4-methoxy-benzyloxy)-2-phenylselanyl-tetrahydro-pyran-4-yl ester

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Chemical Property of Acetic acid (2S,3R,4S,5R)-3-acetoxy-5-(4-methoxy-benzyloxy)-2-phenylselanyl-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5R)-3-acetoxy-5-(4-methoxy-benzyloxy)-2-phenylselanyl-tetrahydro-pyran-4-yl ester

There total 1 articles about Acetic acid (2S,3R,4S,5R)-3-acetoxy-5-(4-methoxy-benzyloxy)-2-phenylselanyl-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: 90.0%

: 645-96-5
Benzeneselenol

: Acetic acid (3R,4S,5R)-4-acetoxy-5-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

: 273918-24-4
Acetic acid (2S,3R,4S,5R)-3-acetoxy-5-(4-methoxy-benzyloxy)-2-phenylselanyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 2h;
DOI:10.1002/(SICI)1521-3773(20000317)39:6<1089::AID-ANIE1089>3.0.CO;2-V DOI:10.1002/1521-3765(20000901)6:17<3166::AID-CHEM3166>3.0.CO;2-Z

Reference yield: 95.0%

: 273918-24-4
Acetic acid (2S,3R,4S,5R)-3-acetoxy-5-(4-methoxy-benzyloxy)-2-phenylselanyl-tetrahydro-pyran-4-yl ester

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

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:

: 273918-24-4
Acetic acid (2S,3R,4S,5R)-3-acetoxy-5-(4-methoxy-benzyloxy)-2-phenylselanyl-tetrahydro-pyran-4-yl ester

: C₂₁H₂₈O₈

Guidance literature:: Multi-step reaction with 9 steps

1: 95 percent / NaOMe; MeOH / 3 h / 25 °C

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

3: 100 percent / DAST / CH₂Cl₂ / 0.5 h / 0 °C

4: 45 percent / SnCl₂; molecular sieves 4 Angstroem / diethyl ether / 3 h / 0 - 25 °C

5: 90 percent / TBAF; AcOH / tetrahydrofuran / 3 h / 25 °C

6: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 - 25 °C

7: 75 percent / NaOMe; MeOH / 1 h / 25 °C

8: 95 percent / aq. NaIO₄ / methanol; CH₂Cl₂ / 1 h / 25 °C

9: iPr₂NH; vinyl acetate / toluene / 12 h / 140 °C

With 2,6-dimethylpyridine; methanol; dmap; sodium periodate; vinyl acetate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; acetic acid; triethylamine; diisopropylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 1: Deacetylation / 2: Etherification / 3: Rearrangement / 4: Glycosidation / 5: Silyl ether cleavage / 6: Esterification / 7: Deacylation / 8: Oxidation / 9: Cyclization;
DOI:10.1002/1521-3765(20000901)6:17<3166::AID-CHEM3166>3.0.CO;2-Z