methyl 2-azido-4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-altropyranoside

Base Information

• Chemical Name: methyl 2-azido-4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-altropyranoside
• CAS No.: 53437-74-4
• Molecular Formula: C₁₄H₁₆BrN₃O₅
• Molecular Weight: 386.202
• Mol file: 53437-74-4.mol

Synonyms:methyl 2-azido-4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-altropyranoside

Chemical Property of methyl 2-azido-4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-altropyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-azido-4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-altropyranoside

There total 2 articles about methyl 2-azido-4-O-benzoyl-6-bromo-2,6-dideoxy-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: 90.0%

methyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-altropyranoside (17460-37-6) → methyl 2-azido-4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-altropyranoside (53437-74-4)

Guidance literature:

With N-Bromosuccinimide; calcium carbonate; In tetrachloromethane; for 1h; Heating;

Reference yield: 87.0%

2-azido-2-deoxy-4,6-O-(phenylmethylene)methyl-α-D-altropyranoside (116003-77-1) → methyl 2-azido-4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-altropyranoside (53437-74-4)

Guidance literature:

With N-Bromosuccinimide; calcium carbonate; In tetrachloromethane; at 80 ℃;

DOI:10.1016/S0040-4020(01)87223-9

Reference yield:

methyl 2-azido-4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-altropyranoside (53437-74-4) → 1S-(1α,4α,5β,6β) 4-azido-5,6-bis<(4-methoxyphenyl)methoxy>-1-benzoyl-2-cyclohexene (153165-88-9)

Guidance literature:

Multi-step reaction with 6 steps

1: MeONa / methanol

2: NaH / dimethylformamide

3: 74 percent / Hg(CF₃CO₂)2 / acetone; H₂O / 20 °C

4: 60 percent / mesyl chloride, pyridine / CH₂Cl₂

5: 76 percent / NaBH₄, CeCl₃*7H₂O / methanol

6: 83 percent / PPh₃, DEAD / tetrahydrofuran / Ambient temperature

With pyridine; sodium tetrahydroborate; cerium(III) chloride; Hg(II) trifluoroacetate; sodium methylate; sodium hydride; methanesulfonyl chloride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)87223-9

upstream raw materials:

methyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-altropyranoside

2-azido-2-deoxy-4,6-O-(phenylmethylene)methyl-α-D-altropyranoside

Downstream raw materials:

1R-(1β,4α,5β,6β) 4-azido-5,6-bis<(4-methoxyphenyl)methoxy>-2-cyclohexen-1-ol

4R-(4α,5β,6β) 4-azido-5,6-bis<(4-methoxyphenyl)methoxy>-2-cyclohexen-1-one

2S-(2β,3β,4α,5α) 4-azido-5-hydroxy-2,3-bis<(4-methoxyphenyl)methoxy>-cyclohexanone

1S-(1α,4α,5β,6β) 4-azido-5,6-bis<(4-methoxyphenyl)methoxy>-1-benzoyl-2-cyclohexene