tert-butyl (Z)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enonate

Base Information

Chemical Name:tert-butyl (Z)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enonate
CAS No.:1305317-71-8
Molecular Formula:C₂₈H₃₆O₆
Molecular Weight:468.59
Hs Code.:

Synonyms:tert-butyl (Z)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enonate

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Chemical Property of tert-butyl (Z)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enonate

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Technology Process of tert-butyl (Z)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enonate

There total 1 articles about tert-butyl (Z)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enonate 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: 57.0%

: tert-butyl 5,7-di-O-benzyl-2,3-dideoxy-D-xylohept-2-enonate

: 77-76-9
2,2-dimethoxy-propane

: 1305317-71-8
tert-butyl (Z)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enonate

: 1037290-72-4
tert-butyl (E)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enonate

Guidance literature:: With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 1.5h;
DOI:10.1016/j.bmc.2011.02.028

Reference yield: 85.0%

: 1305317-71-8
tert-butyl (Z)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enonate

: 1305317-72-9
(Z)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enitol

Guidance literature:: tert-butyl (Z)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enonate; With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -50 - 20 ℃;

With water; In tetrahydrofuran; toluene; at 20 ℃;
DOI:10.1016/j.bmc.2011.02.028

Reference yield:

: 1305317-71-8
tert-butyl (Z)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enonate

: 1305317-75-2
5,7-di-O-benzyl-4,6-O-isopropylidene-D-glycero-L-gulo-heptitol

: 1305317-74-1
5,7-di-O-benzyl-4,6-O-isopropylidene-D-glycero-L-talo-heptitol

Guidance literature:: Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / -50 - 20 °C

1.2: 20 °C

2.1: AD-mix-β; methanesulfonamide / water; tert-butyl alcohol / 48 h / 20 °C

With methanesulfonamide; AD-mix-β; diisobutylaluminium hydride; In tetrahydrofuran; water; toluene; tert-butyl alcohol; 2.1: Sharpless dihydroxylation;
DOI:10.1016/j.bmc.2011.02.028