1-O-allyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-idopyranose

Base Information

Chemical Name:1-O-allyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-idopyranose
CAS No.:867258-74-0
Molecular Formula:C₄₀H₄₈O₅Si
Molecular Weight:636.904
Hs Code.:

Synonyms:1-O-allyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-idopyranose

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Chemical Property of 1-O-allyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-idopyranose

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Technology Process of 1-O-allyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-idopyranose

There total 6 articles about 1-O-allyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-idopyranose 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: 73.2%

: 867258-71-7
1,2-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-β-D-idopyranose

: 107-18-6
allyl alcohol

: 867258-74-0
1-O-allyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-idopyranose

Guidance literature:: With trifluorormethanesulfonic acid; at 20 ℃; for 3.5h;
DOI:10.1016/j.tetasy.2005.07.010

Reference yield:

: 867258-70-6
3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-β-D-idopyranose

: 867258-74-0
1-O-allyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-idopyranose

Guidance literature:: Multi-step reaction with 2 steps

1.1: pyridinium p-toluenesulfonate; Et₃N; (MeO)3CCH₃ / CH₂Cl₂ / 0.67 h / 20 °C

1.2: Et₃N; AcBr / CH₂Cl₂ / 4 h / 20 °C

1.3: 70.7 percent / NaOMe / methanol / 0.5 h / 20 °C

2.1: 73.2 percent / trifluoromethanesulfonic acid / 3.5 h / 20 °C

With Trimethyl orthoacetate; trifluorormethanesulfonic acid; pyridinium p-toluenesulfonate; triethylamine; In dichloromethane;
DOI:10.1016/j.tetasy.2005.07.010

Reference yield:

: 867258-77-3
6-O-(tert-butyldiphenyl)silyl-1,2-di-O-(methoxymethyl)-5a-carba-β-D-idopyranose

: 867258-74-0
1-O-allyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-idopyranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 0 - 20 °C

1.2: 78 percent / Bu₄NI / tetrahydrofuran / 24 h / 20 °C

2.1: 69 percent / molecular sieves 4 Angstroem; TMSBr / CH₂Cl₂ / 2 h / -20 °C

3.1: pyridinium p-toluenesulfonate; Et₃N; (MeO)3CCH₃ / CH₂Cl₂ / 0.67 h / 20 °C

3.2: Et₃N; AcBr / CH₂Cl₂ / 4 h / 20 °C

3.3: 70.7 percent / NaOMe / methanol / 0.5 h / 20 °C

4.1: 73.2 percent / trifluoromethanesulfonic acid / 3.5 h / 20 °C

With Trimethyl orthoacetate; trimethylsilyl bromide; trifluorormethanesulfonic acid; 4 A molecular sieve; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetasy.2005.07.010