Benzoic acid (2R,3R,4R)-3-(4-bromo-benzyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4R)-3-(4-bromo-benzyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester
• CAS No.: 124581-41-5
• Molecular Formula: C₂₆H₃₃BrO₅Si
• Molecular Weight: 533.535
• Mol file: 124581-41-5.mol

Synonyms:

Chemical Property of Benzoic acid (2R,3R,4R)-3-(4-bromo-benzyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3R,4R)-3-(4-bromo-benzyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester

There total 6 articles about Benzoic acid (2R,3R,4R)-3-(4-bromo-benzyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-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:

6-((tert-butyldimethylsilyl)oxy)-3-O-benzoyl-D-galactal (124648-31-3) + 1-bromomethyl-4-bromobenzene (589-15-1) → Benzoic acid (2R,3R,4R)-3-(4-bromo-benzyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester (124581-41-5)

Guidance literature:

With potassium hydride; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 0 ℃; for 1.5h;

DOI:10.1021/jo00290a014

Reference yield:

1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose (3068-32-4) → Benzoic acid (2R,3R,4R)-3-(4-bromo-benzyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester (124581-41-5)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; ammonia; potassium hydride; zinc; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; acetic acid;

DOI:10.1021/jo00290a014

Reference yield:

(2R,3R,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol (124751-19-5) → Benzoic acid (2R,3R,4R)-3-(4-bromo-benzyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester (124581-41-5)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine; potassium hydride; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/jo00290a014

upstream raw materials:

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

1-bromomethyl-4-bromobenzene

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

(2R,3R,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol

Downstream raw materials:

4-O-(4'-bromobenzyl)-6-O-(tert-butyldimethylsilyl)-D-galactal

(E)-(R)-1-[(2R,3aS,5R,6R,7aS)-6-(4-Bromo-benzyloxy)-2-methoxy-hexahydro-furo[3,2-b]pyran-5-yl]-pent-3-en-2-ol

(1S,3R,4R,6S,8R)-4-<(4'-bromobenzyl)oxy>-3-<2(S)-hydroxy-3(E)-pentenyl>-8-(methyloxy)-2,7-dioxabicyclo<4.3.0>nonane

(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