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

Base Information

Chemical Name:1,6-di-O-acetyl-2,4-di-O-benzyl-3-O-(tert-butyldiphenylsilyl)α-D-mannopyranose
CAS No.:277757-03-6
Molecular Formula:C₄₀H₄₆O₈Si
Molecular Weight:682.886
Hs Code.:

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

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

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

There total 6 articles about 1,6-di-O-acetyl-2,4-di-O-benzyl-3-O-(tert-butyldiphenylsilyl)α-D-mannopyranose 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: 89.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 277757-02-5
1,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranose

: 277757-03-6
1,6-di-O-acetyl-2,4-di-O-benzyl-3-O-(tert-butyldiphenylsilyl)α-D-mannopyranose

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 25 ℃; for 17h;
DOI:10.1002/(SICI)1099-0690(200004)2000:8<1547::AID-EJOC1547<3.0.CO;2-C

Reference yield:

: 100-39-0
benzyl bromide

: 277757-03-6
1,6-di-O-acetyl-2,4-di-O-benzyl-3-O-(tert-butyldiphenylsilyl)α-D-mannopyranose

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; sodium hydride; trifluoroacetic acid; dmap; In dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: Ring cleavage / 3: Decomposition / 4: silylation;
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

: 277757-03-6
1,6-di-O-acetyl-2,4-di-O-benzyl-3-O-(tert-butyldiphenylsilyl)α-D-mannopyranose

Guidance literature:: Multi-step reaction with 5 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

With 1H-imidazole; 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;
DOI:10.1002/(SICI)1099-0690(200004)2000:8<1547::AID-EJOC1547<3.0.CO;2-C