allyl 2-azido-3-O-benzyl-2-C-(tert-butyldiphenylsilyloxymethyl)-2-deoxy-α-D-mannopyranoside

Base Information

Chemical Name:allyl 2-azido-3-O-benzyl-2-C-(tert-butyldiphenylsilyloxymethyl)-2-deoxy-α-D-mannopyranoside
CAS No.:344615-44-7
Molecular Formula:C₃₃H₄₁N₃O₆Si
Molecular Weight:603.791
Hs Code.:

Synonyms:allyl 2-azido-3-O-benzyl-2-C-(tert-butyldiphenylsilyloxymethyl)-2-deoxy-α-D-mannopyranoside

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Chemical Property of allyl 2-azido-3-O-benzyl-2-C-(tert-butyldiphenylsilyloxymethyl)-2-deoxy-α-D-mannopyranoside

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Technology Process of allyl 2-azido-3-O-benzyl-2-C-(tert-butyldiphenylsilyloxymethyl)-2-deoxy-α-D-mannopyranoside

There total 6 articles about allyl 2-azido-3-O-benzyl-2-C-(tert-butyldiphenylsilyloxymethyl)-2-deoxy-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:

: ((2R,4aR,6S,7S,8R,8aS)-6-Allyloxy-7-azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ylmethoxy)-tert-butyl-diphenyl-silane

: 344615-44-7
allyl 2-azido-3-O-benzyl-2-C-(tert-butyldiphenylsilyloxymethyl)-2-deoxy-α-D-mannopyranoside

Guidance literature:: With camphor-10-sulfonic acid; In methanol; at 20 ℃; for 26h;
DOI:10.1016/S0040-4039(01)00246-5

Reference yield:

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

: 344615-44-7
allyl 2-azido-3-O-benzyl-2-C-(tert-butyldiphenylsilyloxymethyl)-2-deoxy-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 7 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

6: imidazole / dimethylformamide / 17 h / 20 - 60 °C

7: 15.8 g / camphorsulfonic acid / methanol; tetrahydrofuran / 26 h / 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; sodium azide; oxalyl dichloride; 15-crown-5; camphor-10-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Swern oxidation;
DOI:10.1016/S0040-4020(02)01058-X

Reference yield:

: 228565-56-8
allyl 3-O-benzyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose

: 344615-44-7
allyl 2-azido-3-O-benzyl-2-C-(tert-butyldiphenylsilyloxymethyl)-2-deoxy-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 80 percent / BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2: 1.8-diazabicyclo[5.4.0]undec-7-ene / dimethylsulfoxide / 3 h / 0 °C

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

4: 30.7 g / NaBH₄ / methanol / 1.5 h / 0 °C

5: imidazole / dimethylformamide / 17 h / 20 - 60 °C

6: 15.8 g / camphorsulfonic acid / methanol; tetrahydrofuran / 26 h / 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; sodium azide; 15-crown-5; camphor-10-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; hexane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)01058-X