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

Base Information

Chemical Name: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
CAS No.:306937-80-4
Molecular Formula:C₂₉H₃₇ClO₁₀Se
Molecular Weight:660.02
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 7 articles about 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 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%

: 306937-72-4
Chloro-acetic acid (2R,3R,4S,5R,6S)-3-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-5,6-dimethoxy-2-methyl-tetrahydro-pyran-4-yl ester

: 306937-80-4
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

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 25 ℃; for 3h;
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

: 306937-80-4
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

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

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

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

: 306937-80-4
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

Guidance literature:: Multi-step reaction with 2 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

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