methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside

Base Information

• Chemical Name: methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside
• CAS No.: 299410-97-2
• Molecular Formula: C₂₃H₃₇BrO₇Si
• Molecular Weight: 533.532
• Mol file: 299410-97-2.mol

Synonyms:methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside

Chemical Property of methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside

There total 5 articles about methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside 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: 91.0%

methyl 4,6-O-benzylidene-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-α-D-altropyranoside (299410-95-0) → methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside (299410-97-2)

Guidance literature:

With N-Bromosuccinimide; barium carbonate; In tetrachloromethane; Heating;

DOI:10.1021/jo0491051

Reference yield: 74.0%

→ methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside (299410-97-2)

Guidance literature:

Reference yield:

methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside (299410-93-8) → methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside (299410-97-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.1 g / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

2: 91 percent / BaCO₃; NBS / CCl₄ / Heating

With dmap; N-Bromosuccinimide; triethylamine; barium carbonate; In tetrachloromethane; dichloromethane;

DOI:10.1021/jo0491051

upstream raw materials:

methyl 4,6-O-benzylidene-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-α-D-altropyranoside

tert-butyldimethylsilyl chloride

methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside

Downstream raw materials:

Eldecalcitol

(3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene

(R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

(2R,3S,4R)-4-benzoyloxy-3-[3-(tert-butyldimethylsilyloxy)propoxy]hex-5-ene-1,2-diol