3-O-(6'-azido-2',3',4'-tri-O-benzoyl-6'-deoxy-α-D-mannopyranosyl)-1,2-isopropylidene-sn-glycerol

Base Information

Chemical Name:3-O-(6'-azido-2',3',4'-tri-O-benzoyl-6'-deoxy-α-D-mannopyranosyl)-1,2-isopropylidene-sn-glycerol
CAS No.:1473360-01-8
Molecular Formula:C₃₃H₃₃N₃O₁₀
Molecular Weight:631.639
Hs Code.:

Synonyms:3-O-(6'-azido-2',3',4'-tri-O-benzoyl-6'-deoxy-α-D-mannopyranosyl)-1,2-isopropylidene-sn-glycerol

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Chemical Property of 3-O-(6'-azido-2',3',4'-tri-O-benzoyl-6'-deoxy-α-D-mannopyranosyl)-1,2-isopropylidene-sn-glycerol

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Technology Process of 3-O-(6'-azido-2',3',4'-tri-O-benzoyl-6'-deoxy-α-D-mannopyranosyl)-1,2-isopropylidene-sn-glycerol

There total 7 articles about 3-O-(6'-azido-2',3',4'-tri-O-benzoyl-6'-deoxy-α-D-mannopyranosyl)-1,2-isopropylidene-sn-glycerol 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: 83.0%

: 863915-11-1
6-azido-2,3,4-tri-O-benzoyl-6-deoxy-α-D-mannopyranose-1-O-trichloroacetimidate

: 22323-82-6,36543-79-0
(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol

: 1473360-01-8
3-O-(6'-azido-2',3',4'-tri-O-benzoyl-6'-deoxy-α-D-mannopyranosyl)-1,2-isopropylidene-sn-glycerol

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.5h; Molecular sieve; Inert atmosphere;
DOI:10.1016/j.carres.2013.08.010

Reference yield:

: 1473360-07-4
p-tolyl 6-azido-2,3,4-tri-O-benzoyl-6-deoxy-1-thio-α-D-mannopyranoside

: 1473360-01-8
3-O-(6'-azido-2',3',4'-tri-O-benzoyl-6'-deoxy-α-D-mannopyranosyl)-1,2-isopropylidene-sn-glycerol

Guidance literature:: Multi-step reaction with 3 steps

1: water; N-Bromosuccinimide / acetone / 0.5 h

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 °C

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 °C / Molecular sieve; Inert atmosphere

With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetone;
DOI:10.1016/j.carres.2013.08.010

Reference yield:

: 210170-40-4
1,2,3,4-tetra-O-acetyl-6-azido-6-deoxy-α-D-mannopyranoside

: 1473360-01-8
3-O-(6'-azido-2',3',4'-tri-O-benzoyl-6'-deoxy-α-D-mannopyranosyl)-1,2-isopropylidene-sn-glycerol

Guidance literature:: Multi-step reaction with 6 steps

1: boron trifluoride diethyl etherate / dichloromethane / 12 h / 20 °C

2: methanol; sodium methylate / 0.5 h / pH 9

3: triethylamine; dmap / dichloromethane / 2 h / 20 °C / pH 9

4: water; N-Bromosuccinimide / acetone / 0.5 h

5: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 °C

6: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 °C / Molecular sieve; Inert atmosphere

With methanol; dmap; N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; water; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; acetone;
DOI:10.1016/j.carres.2013.08.010