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

Base Information

• Chemical Name: methyl (tert-butyldimethylsilyl 4-O-allyl-2-O-benzoyl-3-O-benzyl-L-idopyranosid)uronate
• CAS No.: 717902-56-2
• Molecular Formula: C₃₀H₄₀O₈Si
• Molecular Weight: 556.728

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

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

Chemical Property:

Purity/Quality:

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

There total 3 articles about methyl (tert-butyldimethylsilyl 4-O-allyl-2-O-benzoyl-3-O-benzyl-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: 77.0%

benzoyl chloride (98-88-4) + methyl (tert-butyldimethylsilyl 4-O-allyl-3-O-benzyl-L-idopyranosid)uronate (717902-55-1) → methyl (tert-butyldimethylsilyl 4-O-allyl-2-O-benzoyl-3-O-benzyl-L-idopyranosid)uronate (717902-56-2)

Guidance literature:

With dmap; In dichloromethane;

DOI:10.1021/jo035732z

Reference yield:

(2R,3S,4R,5R)-3-Allyloxy-4-benzyloxy-5,6-dihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester → methyl (tert-butyldimethylsilyl 4-O-allyl-2-O-benzoyl-3-O-benzyl-L-idopyranosid)uronate (717902-56-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 170 mg / imidazole / CH₂Cl₂ / 16 h / -25 °C

2: 77 percent / 4-(dimethylamino)pyridine / CH₂Cl₂

With 1H-imidazole; dmap; In dichloromethane;

DOI:10.1021/jo035732z

Reference yield:

methyl 4-O-allyl-3-O-benzyl-1,2-O-isopropylidene-α-L-idopyranosiduronate (615542-95-5) → methyl (tert-butyldimethylsilyl 4-O-allyl-2-O-benzoyl-3-O-benzyl-L-idopyranosid)uronate (717902-56-2)

Guidance literature:

Multi-step reaction with 3 steps

1: trifluoroacetic acid / 0.5 h

2: 170 mg / imidazole / CH₂Cl₂ / 16 h / -25 °C

3: 77 percent / 4-(dimethylamino)pyridine / CH₂Cl₂

With 1H-imidazole; dmap; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo035732z

upstream raw materials:

benzoyl chloride

methyl (tert-butyldimethylsilyl 4-O-allyl-3-O-benzyl-L-idopyranosid)uronate

methyl 4-O-allyl-3-O-benzyl-1,2-O-isopropylidene-α-L-idopyranosiduronate

Downstream raw materials:

(2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-4-Acetoxy-2-acetoxymethyl-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yloxy)-3-allyloxy-5-benzoyloxy-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosiduronate-(1->4)-3,6-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

methyl 4-O-allyl-2-O-benzoyl-3-O-benzyl-L-idopyranosiduronate trichloroacetimidate

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