Benzoic acid (2R,3S,4S,5R)-2-((2R,3S,4S,5R,6S)-4-hydroxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Benzoic acid (2R,3S,4S,5R)-2-((2R,3S,4S,5R,6S)-4-hydroxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yl ester
CAS No.:306937-76-8
Molecular Formula:C₃₄H₄₀O₁₀Se
Molecular Weight:687.646
Hs Code.:

Benzoic acid (2R,3S,4S,5R)-2-((2R,3S,4S,5R,6S)-4-hydroxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yl ester

Synonyms:Benzoic acid (2R,3S,4S,5R)-2-((2R,3S,4S,5R,6S)-4-hydroxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yl ester

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Chemical Property of Benzoic acid (2R,3S,4S,5R)-2-((2R,3S,4S,5R,6S)-4-hydroxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yl ester

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Technology Process of Benzoic acid (2R,3S,4S,5R)-2-((2R,3S,4S,5R,6S)-4-hydroxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yl ester

There total 10 articles about Benzoic acid (2R,3S,4S,5R)-2-((2R,3S,4S,5R,6S)-4-hydroxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yloxy)-5-(4-methoxy-benzyloxy)-3-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: 93.0%

: 306937-82-6
Benzoic acid (2R,3S,4S,5R)-2-[(2R,3R,4S,5R,6S)-4-(2-chloro-acetoxy)-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yloxy]-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yl ester

: 306937-76-8
Benzoic acid (2R,3S,4S,5R)-2-((2R,3S,4S,5R,6S)-4-hydroxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With methanol; sodium methylate; at 25 ℃; for 1h;
DOI:10.1002/1521-3765(20000901)6:17<3166::AID-CHEM3166>3.0.CO;2-Z

Reference yield:

: 98-88-4
benzoyl chloride

: 306937-76-8
Benzoic acid (2R,3S,4S,5R)-2-((2R,3S,4S,5R,6S)-4-hydroxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 - 25 °C

2: 93 percent / NaOMe; MeOH / 1 h / 25 °C

With methanol; dmap; sodium methylate; triethylamine; In dichloromethane; 1: Esterification / 2: Deacylation;
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

: 306937-76-8
Benzoic acid (2R,3S,4S,5R)-2-((2R,3S,4S,5R,6S)-4-hydroxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 6 steps

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

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

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

4: 93 percent / TBAF; AcOH / tetrahydrofuran / 3 h / 25 °C

5: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 - 25 °C

6: 93 percent / NaOMe; MeOH / 1 h / 25 °C

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