methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-altropyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-altropyranoside
• CAS No.: 85982-95-2
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.386

Synonyms:methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-altropyranoside

Chemical Property of methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-altropyranoside

Chemical Property:

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Technology Process of methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-altropyranoside

There total 1 articles about methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-altropyranoside 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: 75.0%

(4aR,6S,7R,8aR)-6-Methoxy-7-(2-methyl-allyl)-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one → methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-altropyranoside (85982-95-2) + methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methylallyl)-α-D-mannopyranoside

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jo020362k

Reference yield: 95.0%

methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-altropyranoside (85982-95-2) → (4aR,6S,7R,8aR)-6-Methoxy-7-(2-methyl-allyl)-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

Guidance literature:

With dimethyl sulfoxide; trifluoroacetic anhydride;

DOI:10.1021/jo020362k

Reference yield:

methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-altropyranoside (85982-95-2) → methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methylallyl)-α-D-mannopyranoside

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / DMSO; TFAA

2: 75 percent / DIBAL / tetrahydrofuran / 2 h / 20 °C

With diisobutylaluminium hydride; dimethyl sulfoxide; trifluoroacetic anhydride; In tetrahydrofuran;

DOI:10.1021/jo020362k

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