methyl O-[2-O-benzoyl-4-O-levulinyl-3-O-methyl-6-O-(tert-butyldimethylsilyl)-α-L-idopyranosyl]-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside

Base Information

Chemical Name:methyl O-[2-O-benzoyl-4-O-levulinyl-3-O-methyl-6-O-(tert-butyldimethylsilyl)-α-L-idopyranosyl]-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside
CAS No.:189390-21-4
Molecular Formula:C₄₇H₆₄O₁₄Si
Molecular Weight:881.102
Hs Code.:

Synonyms:methyl O-[2-O-benzoyl-4-O-levulinyl-3-O-methyl-6-O-(tert-butyldimethylsilyl)-α-L-idopyranosyl]-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside

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Chemical Property of methyl O-[2-O-benzoyl-4-O-levulinyl-3-O-methyl-6-O-(tert-butyldimethylsilyl)-α-L-idopyranosyl]-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside

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Technology Process of methyl O-[2-O-benzoyl-4-O-levulinyl-3-O-methyl-6-O-(tert-butyldimethylsilyl)-α-L-idopyranosyl]-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside

There total 8 articles about methyl O-[2-O-benzoyl-4-O-levulinyl-3-O-methyl-6-O-(tert-butyldimethylsilyl)-α-L-idopyranosyl]-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside 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:

: 76375-66-1
methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

: 189390-21-4
methyl O-[2-O-benzoyl-4-O-levulinyl-3-O-methyl-6-O-(tert-butyldimethylsilyl)-α-L-idopyranosyl]-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 79 percent / NaH / dimethylformamide / 1 h

2: 70 percent / HBF₄, NaBH₃CN / tetrahydrofuran; diethyl ether / 1.25 h

3: 89 percent / triflic acid, N-iodosuccinimide, 4A molecular sieves / toluene / 1 h

4: aq. CF₃CO₂H / CH₂Cl₂ / 0.67 h / Ambient temperature

5: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 50 °C

6: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h

With dmap; N-iodo-succinimide; tetrafluoroboric acid; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium hydride; sodium cyanoborohydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm960726z

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 189390-21-4
methyl O-[2-O-benzoyl-4-O-levulinyl-3-O-methyl-6-O-(tert-butyldimethylsilyl)-α-L-idopyranosyl]-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 50 °C

2: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h

With dmap; triethylamine; In dichloromethane;
DOI:10.1021/jm960726z

Reference yield:

: ethyl 2-O-benzoyl-4,6-O-isopropylidene-3-O-methyl-1-thio-L-idopyranoside

: 189390-21-4
methyl O-[2-O-benzoyl-4-O-levulinyl-3-O-methyl-6-O-(tert-butyldimethylsilyl)-α-L-idopyranosyl]-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / triflic acid, N-iodosuccinimide, 4A molecular sieves / toluene / 1 h

2: aq. CF₃CO₂H / CH₂Cl₂ / 0.67 h / Ambient temperature

3: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 50 °C

4: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; triethylamine; trifluoroacetic acid; In dichloromethane; toluene;
DOI:10.1021/jm960726z