ethyl 2,2-difluoro-2-(3,4,6-tri-O-benzyl-α-D-arabino-hexopyranosid-2-ulosyl)acetate

Base Information

• Chemical Name: ethyl 2,2-difluoro-2-(3,4,6-tri-O-benzyl-α-D-arabino-hexopyranosid-2-ulosyl)acetate
• CAS No.: 944733-22-6
• Molecular Formula: C₃₁H₃₂F₂O₇
• Molecular Weight: 554.588

Synonyms:ethyl 2,2-difluoro-2-(3,4,6-tri-O-benzyl-α-D-arabino-hexopyranosid-2-ulosyl)acetate

Chemical Property of ethyl 2,2-difluoro-2-(3,4,6-tri-O-benzyl-α-D-arabino-hexopyranosid-2-ulosyl)acetate

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Technology Process of ethyl 2,2-difluoro-2-(3,4,6-tri-O-benzyl-α-D-arabino-hexopyranosid-2-ulosyl)acetate

There total 1 articles about ethyl 2,2-difluoro-2-(3,4,6-tri-O-benzyl-α-D-arabino-hexopyranosid-2-ulosyl)acetate 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:

2,3,4,6-tetra-O-benzyl 1,5-anhydro-D-arabino-hex-1-enitol (4132-26-7) + Ethyl bromodifluoroacetate (667-27-6) → ethyl 2,2-difluoro-2-(3,4,6-tri-O-benzyl-α-D-arabino-hexopyranosid-2-ulosyl)acetate (944733-22-6) + ethyl 2,2-difluoro-2-(3,4,6-tri-O-benzyl-β-D-arabino-hexopyranosid-2-ulosyl)acetate (944733-23-7)

Guidance literature:

With triethyl borane; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 60h;

DOI:10.1021/ol070835f

Reference yield: 68.0%

ethyl 2,2-difluoro-2-(3,4,6-tri-O-benzyl-α-D-arabino-hexopyranosid-2-ulosyl)acetate (944733-22-6) → 2,2-difluoro-2-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)ethanol

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃;

DOI:10.1021/ol070835f

Reference yield: 58.0%

ethyl 2,2-difluoro-2-(3,4,6-tri-O-benzyl-α-D-arabino-hexopyranosid-2-ulosyl)acetate (944733-22-6) → ethyl 2,2-difluoro-2-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)acetate (944733-27-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; at -78 ℃; for 1.5h;

DOI:10.1021/ol070835f

upstream raw materials:

2,3,4,6-tetra-O-benzyl 1,5-anhydro-D-arabino-hex-1-enitol

Ethyl bromodifluoroacetate

Downstream raw materials:

ethyl 2,2-difluoro-2-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)acetate

ethyl 2,2-difluoro-2-(3,4,6-tri-O-benzyl-β-D-arabino-hexopyranosid-2-ulosyl)acetate

ethyl 2,2-difluoro-2-(2-O-methoxymethyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)acetate

ethyl 4,5-difluoro-4-(2-O-methoxymethyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)but-2-enoate

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