(3aS,5R,6S,7R,7aR)-6-(4-Bromo-benzyloxy)-5-hydroxymethyl-7-phenylselanyl-hexahydro-furo[3,2-b]pyran-2-one

Base Information

Chemical Name:(3aS,5R,6S,7R,7aR)-6-(4-Bromo-benzyloxy)-5-hydroxymethyl-7-phenylselanyl-hexahydro-furo[3,2-b]pyran-2-one
CAS No.:124581-46-0
Molecular Formula:C₂₁H₂₁BrO₅Se
Molecular Weight:512.259
Hs Code.:

Synonyms:(3aS,5R,6S,7R,7aR)-6-(4-Bromo-benzyloxy)-5-hydroxymethyl-7-phenylselanyl-hexahydro-furo[3,2-b]pyran-2-one

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Chemical Property of (3aS,5R,6S,7R,7aR)-6-(4-Bromo-benzyloxy)-5-hydroxymethyl-7-phenylselanyl-hexahydro-furo[3,2-b]pyran-2-one

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Technology Process of (3aS,5R,6S,7R,7aR)-6-(4-Bromo-benzyloxy)-5-hydroxymethyl-7-phenylselanyl-hexahydro-furo[3,2-b]pyran-2-one

There total 9 articles about (3aS,5R,6S,7R,7aR)-6-(4-Bromo-benzyloxy)-5-hydroxymethyl-7-phenylselanyl-hexahydro-furo[3,2-b]pyran-2-one 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: 85.5%

: 5707-04-0
Phenylselenyl chloride

: 124581-43-7
N,N-dimethyl-(2S,5R,6R)-5-<(4'-bromobenzyl)oxy>-6-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-3,4-dideoxypyran-2-acetamide

: 124581-46-0
(3aS,5R,6S,7R,7aR)-6-(4-Bromo-benzyloxy)-5-hydroxymethyl-7-phenylselanyl-hexahydro-furo[3,2-b]pyran-2-one

: 124581-45-9
(1S,3R,4S,5R,6R)-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-<(4'-bromobenzyl)oxy>-5-(phenylseleno)-2,7-dioxabicyclo<4.3.0>nonan-8-one

: 124581-44-8
(3aR,5R,6S,7R,7aR)-6-(4-Bromo-benzyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-bis-phenylselanyl-hexahydro-furo[3,2-b]pyran-2-one

Guidance literature:: In dichloromethane; at -78 ℃; for 2h;
DOI:10.1021/jo00290a014

Reference yield:

: 3068-32-4
1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose

: 124581-46-0
(3aS,5R,6S,7R,7aR)-6-(4-Bromo-benzyloxy)-5-hydroxymethyl-7-phenylselanyl-hexahydro-furo[3,2-b]pyran-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: zinc dust / aq. acetic acid / 1 h / 0 °C

2: NH₃ / methanol / 15 h / Ambient temperature

3: 73 percent / pyridine / 1) 0 deg C, 1 h, 2) RT, 15 h

4: 95 percent / pyridine / 1) - 35 deg C, 1.5 h, 2) up to 0 deg C, 30 min

5: KH / hexamethylphosphoric acid triamide / 1.5 h / 0 °C

6: 10percent aq. NaOH / methanol / 15 h / Ambient temperature

7: 95 percent / xylene / 10 h / 142 °C

8: 4.4 percent / CH₂Cl₂ / 2 h / -78 °C

With pyridine; sodium hydroxide; ammonia; potassium hydride; zinc; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetic acid; xylene;
DOI:10.1021/jo00290a014

Reference yield:

: 124648-31-3
6-((tert-butyldimethylsilyl)oxy)-3-O-benzoyl-D-galactal

: 124581-46-0
(3aS,5R,6S,7R,7aR)-6-(4-Bromo-benzyloxy)-5-hydroxymethyl-7-phenylselanyl-hexahydro-furo[3,2-b]pyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: KH / hexamethylphosphoric acid triamide / 1.5 h / 0 °C

2: 10percent aq. NaOH / methanol / 15 h / Ambient temperature

3: 95 percent / xylene / 10 h / 142 °C

4: 4.4 percent / CH₂Cl₂ / 2 h / -78 °C

With sodium hydroxide; potassium hydride; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; xylene;
DOI:10.1021/jo00290a014