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

Base Information

• Chemical Name: methyl (tert-butyldimethylsilyl 4-O-allyl-3-O-benzyl-L-idopyranosid)uronate
• CAS No.: 717902-55-1
• Molecular Formula: C₂₃H₃₆O₇Si
• Molecular Weight: 452.62

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

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

Chemical Property:

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

There total 2 articles about methyl (tert-butyldimethylsilyl 4-O-allyl-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:

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,3S,4R,5R)-3-Allyloxy-4-benzyloxy-5,6-dihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester → methyl (tert-butyldimethylsilyl 4-O-allyl-3-O-benzyl-L-idopyranosid)uronate (717902-55-1)

Guidance literature:

With 1H-imidazole; In dichloromethane; at -25 ℃; for 16h;

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-3-O-benzyl-L-idopyranosid)uronate (717902-55-1)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / 0.5 h

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

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

DOI:10.1021/jo035732z

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

upstream raw materials:

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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

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

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

(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

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