(2R,3R,4R,5S)-3-Benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-ol

Base Information

Chemical Name:(2R,3R,4R,5S)-3-Benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-ol
CAS No.:306726-25-0
Molecular Formula:C₃₈H₅₂O₉SeSi
Molecular Weight:759.871
Hs Code.:

(2R,3R,4R,5S)-3-Benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-ol

Synonyms:(2R,3R,4R,5S)-3-Benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-ol

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Chemical Property of (2R,3R,4R,5S)-3-Benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-ol

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Technology Process of (2R,3R,4R,5S)-3-Benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-ol

There total 9 articles about (2R,3R,4R,5S)-3-Benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-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: 99.0%

: 306726-24-9
Benzoic acid (2R,3R,4R,5S)-3-benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-yl ester

: 306726-25-0
(2R,3R,4R,5S)-3-Benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-ol

Guidance literature:: With sodium hydroxide; In methanol; at 25 ℃; for 1h;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

: 5707-04-0
Phenylselenyl chloride

: 306726-14-7
(3S,4R,5R,6R)-5-Benzyloxy-6-methoxy-tetrahydro-pyran-3,4-diol

: tert-butyl-[3-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran-4-yloxy]-dimethyl-silane

: 306726-18-1
(3S,4R,5R,6R)-5-Benzyloxy-4-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-6-methoxy-tetrahydro-pyran-3-ol

: 306726-25-0
(2R,3R,4R,5S)-3-Benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-ol

Guidance literature:: Phenylselenyl chloride; tert-butyl-[3-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran-4-yloxy]-dimethyl-silane; In acetonitrile; at 25 ℃; for 0.0833333h;

(3S,4R,5R,6R)-5-Benzyloxy-6-methoxy-tetrahydro-pyran-3,4-diol; With 2,3,5-trimethyl-pyridine; In acetonitrile; at 25 ℃; for 12h; Title compound not separated from byproducts;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 306726-25-0
(2R,3R,4R,5S)-3-Benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / 2,6-lutidine / tetrahydrofuran / 0.5 h / -78 °C

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

3: SnCl₂ / diethyl ether / 3 h / 0 - 25 °C

4: 99 percent / NaOH / methanol / 1 h / 25 °C

With 2,6-dimethylpyridine; sodium hydroxide; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1: Etherification / 2: Rearrangement / 3: Glycosidation / 4: Debenzoylation;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8