allyl 4,6-O-benzylidene-2-benzyloxycarbonylamino-2-deoxy-α-D-ribo-hexapyranosid-3-ulose

Base Information

• Chemical Name: allyl 4,6-O-benzylidene-2-benzyloxycarbonylamino-2-deoxy-α-D-ribo-hexapyranosid-3-ulose
• CAS No.: 128745-42-6
• Molecular Formula: C₂₄H₂₅NO₇
• Molecular Weight: 439.465

Synonyms:allyl 4,6-O-benzylidene-2-benzyloxycarbonylamino-2-deoxy-α-D-ribo-hexapyranosid-3-ulose

Chemical Property of allyl 4,6-O-benzylidene-2-benzyloxycarbonylamino-2-deoxy-α-D-ribo-hexapyranosid-3-ulose

Chemical Property:

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Technology Process of allyl 4,6-O-benzylidene-2-benzyloxycarbonylamino-2-deoxy-α-D-ribo-hexapyranosid-3-ulose

There total 3 articles about allyl 4,6-O-benzylidene-2-benzyloxycarbonylamino-2-deoxy-α-D-ribo-hexapyranosid-3-ulose 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: 97.0%

allyl 4,6-O-benzylidene-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside (128745-41-5) → allyl 4,6-O-benzylidene-2-benzyloxycarbonylamino-2-deoxy-α-D-ribo-hexapyranosid-3-ulose (128745-42-6)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 1.5h;

DOI:10.1016/0008-6215(89)85012-8

Reference yield:

benzyl ((2S,3R,4R,5S,6R)-2-(allyloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate (83663-03-0) → allyl 4,6-O-benzylidene-2-benzyloxycarbonylamino-2-deoxy-α-D-ribo-hexapyranosid-3-ulose (128745-42-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / fused ZnCl₂ / 16 h / Ambient temperature

2: 97 percent / DMSO, oxalyl chloride, Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; zinc(II) chloride; In dichloromethane;

DOI:10.1016/0008-6215(89)85012-8

Reference yield:

benzaldehyde (100-52-7) → allyl 4,6-O-benzylidene-2-benzyloxycarbonylamino-2-deoxy-α-D-ribo-hexapyranosid-3-ulose (128745-42-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / fused ZnCl₂ / 16 h / Ambient temperature

2: 97 percent / DMSO, oxalyl chloride, Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; zinc(II) chloride; In dichloromethane;

DOI:10.1016/0008-6215(89)85012-8

upstream raw materials:

allyl 4,6-O-benzylidene-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

benzyl ((2S,3R,4R,5S,6R)-2-(allyloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate

benzaldehyde

Downstream raw materials:

allyl 4,6-O-benzylidene-2-benzyloxycarbonylamino-2-deoxy-α-D-allopyranoside

1-propenyl 2-amino-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-α-D-allopyranoside

allyl 2-amino-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-α-D-allopyranoside

2-amino-6-O-(tert-butyldiphenylsilyl)-2-N,3-O-carbonyl-deoxy-D-allitol

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