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

Base Information

Chemical Name:ethyl 4,5-difluoro-4-(2-O-methoxymethyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)but-2-enoate
CAS No.:944733-32-8
Molecular Formula:C₃₅H₄₀F₂O₈
Molecular Weight:626.695
Hs Code.:

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

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

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

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

: 944733-27-1
ethyl 2,2-difluoro-2-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)acetate

: 944733-32-8
ethyl 4,5-difluoro-4-(2-O-methoxymethyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)but-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 83 percent / P₂O₅ / CHCl₃ / 0.25 h

2.1: DIBAL-H / toluene / 1 h / -78 °C

2.2: 76 percent / LiBr / Et₃N / tetrahydrofuran / 20 °C

With phosphorus pentoxide; diisobutylaluminium hydride; In chloroform; toluene; 2.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol070835f

Reference yield:

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

: 944733-32-8
ethyl 4,5-difluoro-4-(2-O-methoxymethyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)but-2-enoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 58 percent / NaBH₄ / methanol / 1.5 h / -78 °C

2.1: 83 percent / P₂O₅ / CHCl₃ / 0.25 h

3.1: DIBAL-H / toluene / 1 h / -78 °C

3.2: 76 percent / LiBr / Et₃N / tetrahydrofuran / 20 °C

With sodium tetrahydroborate; phosphorus pentoxide; diisobutylaluminium hydride; In methanol; chloroform; toluene; 3.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol070835f

Reference yield:

: 4132-26-7
2,3,4,6-tetra-O-benzyl 1,5-anhydro-D-arabino-hex-1-enitol

: 944733-32-8
ethyl 4,5-difluoro-4-(2-O-methoxymethyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)but-2-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: BEt₃ / dimethylformamide; tetrahydrofuran / 60 h / 20 °C

2.1: 58 percent / NaBH₄ / methanol / 1.5 h / -78 °C

3.1: 83 percent / P₂O₅ / CHCl₃ / 0.25 h

4.1: DIBAL-H / toluene / 1 h / -78 °C

4.2: 76 percent / LiBr / Et₃N / tetrahydrofuran / 20 °C

With sodium tetrahydroborate; triethyl borane; phosphorus pentoxide; diisobutylaluminium hydride; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide; toluene; 4.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol070835f