allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-mannopyranoside

Base Information

Chemical Name:allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-mannopyranoside
CAS No.:344615-43-6
Molecular Formula:C₂₄H₂₇N₃O₆
Molecular Weight:453.495
Hs Code.:

Synonyms:allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-mannopyranoside

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Chemical Property of allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-mannopyranoside

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Technology Process of allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-mannopyranoside

There total 5 articles about allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-mannopyranoside 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: 84.0%

: 344615-42-5
allyl 3-O-benzyl-4,6-O-benzylidene-2-C-dichloromethyl-α-D-glucopyranoside

: 344615-43-6
allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-mannopyranoside

Guidance literature:: allyl 3-O-benzyl-4,6-O-benzylidene-2-C-dichloromethyl-α-D-glucopyranoside; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 0 ℃; for 3h;

With sodium azide; 15-crown-5; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 70 ℃; for 17h;

With sodium tetrahydroborate; In methanol; at 0 ℃; for 1.5h;
DOI:10.1016/S0040-4039(01)00246-5

Reference yield:

: 500783-31-3
allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-formyl-α-D-mannopyranoside

: 344615-43-6
allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-mannopyranoside

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 1.5h;
DOI:10.1016/S0040-4020(02)01058-X

Reference yield:

: 128241-14-5
allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside

: 344615-43-6
allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 76 percent / oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

2: 80 percent / BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

3: 1.8-diazabicyclo[5.4.0]undec-7-ene / dimethylsulfoxide / 3 h / 0 °C

4: NaN₃; 15-crown-5; hexamethylphosphoric triamide / 17 h / 70 °C

5: 30.7 g / NaBH₄ / methanol / 1.5 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; sodium azide; oxalyl dichloride; 15-crown-5; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; 1: Swern oxidation;
DOI:10.1016/S0040-4020(02)01058-X