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

Base Information

• Chemical Name: 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
• CAS No.: 306937-82-6
• Molecular Formula: C₃₆H₄₁ClO₁₁Se
• Molecular Weight: 764.128

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

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Technology Process of 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

There total 8 articles about 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 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%

benzoyl chloride (98-88-4) + Chloro-acetic acid (2R,3R,4S,5R,6S)-3-[(2R,3S,4S,5R)-4-hydroxy-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-5,6-dimethoxy-2-methyl-tetrahydro-pyran-4-yl ester (306937-80-4) → 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 (306937-82-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 25 ℃; for 3h;

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) → 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 (306937-82-6)

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: 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

With 2,6-dimethylpyridine; dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; 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;

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

Reference yield:

tert-Butyl-[(3S,4S,5R)-2-fluoro-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yloxy]-dimethyl-silane (256341-86-3) → 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 (306937-82-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 45 percent / SnCl₂; molecular sieves 4 Angstroem / diethyl ether / 3 h / 0 - 25 °C

2: 93 percent / TBAF; AcOH / tetrahydrofuran / 3 h / 25 °C

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

With dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; acetic acid; triethylamine; tin(ll) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Glycosidation / 2: Silyl ether cleavage / 3: Esterification;

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

upstream raw materials:

benzoyl chloride

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

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

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

Downstream raw materials:

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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