methyl (benzyl 2-O-benzoyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosid)uronate

Base Information

Chemical Name:methyl (benzyl 2-O-benzoyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosid)uronate
CAS No.:321380-26-1
Molecular Formula:C₃₄H₄₂O₈Si
Molecular Weight:606.788
Hs Code.:

Synonyms:methyl (benzyl 2-O-benzoyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosid)uronate

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Chemical Property of methyl (benzyl 2-O-benzoyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosid)uronate

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Technology Process of methyl (benzyl 2-O-benzoyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosid)uronate

There total 9 articles about methyl (benzyl 2-O-benzoyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosid)uronate 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:

: 79-22-1
methyl chloroformate

: (2R,3S,4R,5R,6R)-5-Benzoyloxy-4,6-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-carboxylic acid

: 321380-26-1
methyl (benzyl 2-O-benzoyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosid)uronate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1016/S0008-6215(00)00234-2

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 321380-26-1
methyl (benzyl 2-O-benzoyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosid)uronate

Guidance literature:: Multi-step reaction with 3 steps

1: 3.74 g / imidazole / dimethylformamide / 18 h / 50 °C

2: CrO₃ / aq. H₂SO₄ / 0 °C

3: 1.73 g / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; chromium(VI) oxide; dmap; triethylamine; In dichloromethane; sulfuric acid; N,N-dimethyl-formamide; 2: Jones oxidation;
DOI:10.1016/S0008-6215(00)00234-2

Reference yield:

: (2R,3R,4S,5R,6S)-2,4-Bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

: 321380-26-1
methyl (benzyl 2-O-benzoyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosid)uronate

Guidance literature:: Multi-step reaction with 6 steps

1: 10-D,L-camphorsulfonic acid / dimethylformamide / 3 h / 0 °C

2: 2.53 g / pyridine / 0.5 h / 20 °C

3: acetic acid; H₂O / 0.25 h / 80 °C

4: 3.74 g / imidazole / dimethylformamide / 18 h / 50 °C

5: CrO₃ / aq. H₂SO₄ / 0 °C

6: 1.73 g / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; chromium(VI) oxide; dmap; (1S)-10-camphorsulfonic acid; triethylamine; In pyridine; dichloromethane; sulfuric acid; water; acetic acid; N,N-dimethyl-formamide; 5: Jones oxidation;
DOI:10.1016/S0008-6215(00)00234-2