4,5-O-carbonylidene-1,2,3-trideoxy-6,7:8,9-di-O-isopropylidene-2-phenyl-D-glycero-D-gulo-non-1-enitol

Base Information

Chemical Name:4,5-O-carbonylidene-1,2,3-trideoxy-6,7:8,9-di-O-isopropylidene-2-phenyl-D-glycero-D-gulo-non-1-enitol
CAS No.:503544-14-7
Molecular Formula:C₂₂H₂₈O₇
Molecular Weight:404.46
Hs Code.:

Synonyms:4,5-O-carbonylidene-1,2,3-trideoxy-6,7:8,9-di-O-isopropylidene-2-phenyl-D-glycero-D-gulo-non-1-enitol

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Chemical Property of 4,5-O-carbonylidene-1,2,3-trideoxy-6,7:8,9-di-O-isopropylidene-2-phenyl-D-glycero-D-gulo-non-1-enitol

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Technology Process of 4,5-O-carbonylidene-1,2,3-trideoxy-6,7:8,9-di-O-isopropylidene-2-phenyl-D-glycero-D-gulo-non-1-enitol

There total 4 articles about 4,5-O-carbonylidene-1,2,3-trideoxy-6,7:8,9-di-O-isopropylidene-2-phenyl-D-glycero-D-gulo-non-1-enitol 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: 92.0%

: 503544-12-5
1,2,3-trideoxy-6,7:8,9-di-O-isopropylidene-2-phenyl-D-glycero-D-gulo-non-1-enitol

: 503-38-8
trichloromethyl chloroformate

: 503544-14-7
4,5-O-carbonylidene-1,2,3-trideoxy-6,7:8,9-di-O-isopropylidene-2-phenyl-D-glycero-D-gulo-non-1-enitol

Guidance literature:: With dmap; In pyridine; dichloromethane; at 0 - 20 ℃; for 0.5h;
DOI:10.1016/S0008-6215(02)00176-3

Reference yield:

: 52492-60-1
1,2:3,4:5,6-tri-O-isopropylidene-δ-gluconolactone

: 503544-14-7
4,5-O-carbonylidene-1,2,3-trideoxy-6,7:8,9-di-O-isopropylidene-2-phenyl-D-glycero-D-gulo-non-1-enitol

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / tetrahydrofuran; diethyl ether / 0.33 h / -95 °C

2: 80 percent / Zn(BH₄)2 / diethyl ether / 1 h / -10 °C

3: 92 percent / DMAP / pyridine; CH₂Cl₂ / 0.5 h / 0 - 20 °C

With dmap; zinc(II) tetrahydroborate; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane;
DOI:10.1016/S0008-6215(02)00176-3

Reference yield:

: α-bromomagnesium methylstyrene

: 503544-14-7
4,5-O-carbonylidene-1,2,3-trideoxy-6,7:8,9-di-O-isopropylidene-2-phenyl-D-glycero-D-gulo-non-1-enitol

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / tetrahydrofuran; diethyl ether / 0.33 h / -95 °C

2: 80 percent / Zn(BH₄)2 / diethyl ether / 1 h / -10 °C

3: 92 percent / DMAP / pyridine; CH₂Cl₂ / 0.5 h / 0 - 20 °C

With dmap; zinc(II) tetrahydroborate; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane;
DOI:10.1016/S0008-6215(02)00176-3