phenyl 6-O-acetyl-2,4-di-O-benzyl-3-O-(tert-butyldiphenylsilyl)-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:phenyl 6-O-acetyl-2,4-di-O-benzyl-3-O-(tert-butyldiphenylsilyl)-1-thio-α-D-mannopyranoside
CAS No.:277757-04-7
Molecular Formula:C₄₄H₄₈O₆SSi
Molecular Weight:733.013
Hs Code.:

Synonyms:phenyl 6-O-acetyl-2,4-di-O-benzyl-3-O-(tert-butyldiphenylsilyl)-1-thio-α-D-mannopyranoside

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Chemical Property of phenyl 6-O-acetyl-2,4-di-O-benzyl-3-O-(tert-butyldiphenylsilyl)-1-thio-α-D-mannopyranoside

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Technology Process of phenyl 6-O-acetyl-2,4-di-O-benzyl-3-O-(tert-butyldiphenylsilyl)-1-thio-α-D-mannopyranoside

There total 8 articles about phenyl 6-O-acetyl-2,4-di-O-benzyl-3-O-(tert-butyldiphenylsilyl)-1-thio-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:

: 100-39-0
benzyl bromide

: 277757-04-7
phenyl 6-O-acetyl-2,4-di-O-benzyl-3-O-(tert-butyldiphenylsilyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / NaH / dimethylformamide / 2 h / 25 °C

2: 79 percent / F₃CSO₃SiMe / 3 h / 0 - 25 °C

3: 98 percent / TFA / CH₂Cl₂ / 3 h / 25 °C

4: 89 percent / imidazole / DMAP / dimethylformamide / 17 h / 25 °C

5: BF₃*Et₂O / CH₂Cl₂ / 30 h / 25 °C

With 1H-imidazole; boron trifluoride diethyl etherate; sodium hydride; trifluoroacetic acid; dmap; In dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: Ring cleavage / 3: Decomposition / 4: silylation / 5: Substitution;
DOI:10.1002/(SICI)1099-0690(200004)2000:8<1547::AID-EJOC1547<3.0.CO;2-C

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 277757-04-7
phenyl 6-O-acetyl-2,4-di-O-benzyl-3-O-(tert-butyldiphenylsilyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 89 percent / imidazole / DMAP / dimethylformamide / 17 h / 25 °C

2: BF₃*Et₂O / CH₂Cl₂ / 30 h / 25 °C

With 1H-imidazole; boron trifluoride diethyl etherate; dmap; In dichloromethane; N,N-dimethyl-formamide; 1: silylation / 2: Substitution;
DOI:10.1002/(SICI)1099-0690(200004)2000:8<1547::AID-EJOC1547<3.0.CO;2-C

Reference yield:

: 93793-97-6
1,6-anhydro-2,3-O-endo-(4-methoxybenzylidene)-β-D-mannopyranose

: 277757-04-7
phenyl 6-O-acetyl-2,4-di-O-benzyl-3-O-(tert-butyldiphenylsilyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 79 percent / DIBALH / CH₂Cl₂; toluene / 5 h / 0 °C

2: 100 percent / NaH / dimethylformamide / 2 h / 25 °C

3: 79 percent / F₃CSO₃SiMe / 3 h / 0 - 25 °C

4: 98 percent / TFA / CH₂Cl₂ / 3 h / 25 °C

5: 89 percent / imidazole / DMAP / dimethylformamide / 17 h / 25 °C

6: BF₃*Et₂O / CH₂Cl₂ / 30 h / 25 °C

With 1H-imidazole; boron trifluoride diethyl etherate; sodium hydride; diisobutylaluminium hydride; trifluoroacetic acid; dmap; In dichloromethane; N,N-dimethyl-formamide; toluene; 1: Hydrogenolysis / 2: Alkylation / 3: Ring cleavage / 4: Decomposition / 5: silylation / 6: Substitution;
DOI:10.1002/(SICI)1099-0690(200004)2000:8<1547::AID-EJOC1547<3.0.CO;2-C