pent-4-enyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: pent-4-enyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 182003-05-0
• Molecular Formula: C₂₈H₃₁NO₈
• Molecular Weight: 509.556

Synonyms:pent-4-enyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of pent-4-enyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property:

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Technology Process of pent-4-enyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 5 articles about pent-4-enyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-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: 79.0%

pent-4-enyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (191482-45-8) → pent-4-enyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (182003-05-0)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran;

DOI:10.1021/jo962362o

Reference yield:

pent-4-enyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside → pent-4-enyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (182003-05-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / pyridine / 2 h

2: 79 percent / NaCNBH₃, HCl / tetrahydrofuran

With pyridine; hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran;

DOI:10.1021/jo962362o

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose (10022-13-6,31505-44-9,81704-02-1,116347-84-3,131234-07-6,144300-04-9,79733-86-1) → pent-4-enyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (182003-05-0)

Guidance literature:

DOI:10.1021/jo961115h

upstream raw materials:

benzaldehyde dimethyl acetal

acetic anhydride

pent-4-enyl 2-deoxy-2-phthalimido-β-D-glucopyranoside

pent-4-enyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

Acetic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-3-amino-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-pent-4-enyloxy-tetrahydro-pyran-4-yl ester

4,5-dibromopentanyl (3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl)-(1-4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

pent-4-enyl (3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl)-(1-4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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