(E)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enitol

Base Information

• Chemical Name: (E)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enitol
• CAS No.: 1037290-74-6
• Molecular Formula: C₂₄H₃₀O₅
• Molecular Weight: 398.499
• Mol file: 1037290-74-6.mol

Synonyms:(E)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enitol

Chemical Property of (E)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enitol

There total 7 articles about (E)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-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: 98.0%

ethyl (4S,5R,6R,2E)-5,7-bis(benzyloxy)-4,6-(isopropylidenedioxy)hept-2-enoate → (E)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enitol (1037290-74-6)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -15 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2015.11.001

Reference yield: 89.0%

tert-butyl (E)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enonate (1037290-72-4) → (E)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enitol (1037290-74-6)

Guidance literature:

tert-butyl (E)-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:

tert-butyl (E)-5,7-di-O-benzyl-2,3-dideoxy-D-xylohept-2-enonate (1037290-71-3) → (E)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-xylo-hept-2-enitol (1037290-74-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene-4-sulfonic acid / acetone / 1.5 h / 20 °C

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

2.2: 20 °C

With diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; acetone; toluene;

DOI:10.1016/j.bmc.2011.02.028

upstream raw materials:

tert-butyl (E)-5,7-di-O-benzyl-2,3-dideoxy-D-xylohept-2-enonate

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

3,5-di-O-benzyl-D-xylofuranose

Downstream raw materials:

5,7-di-O-benzyl-4,6-O-isopropylidene-D-glycero-L-galacto-heptitol

5,7-di-O-benzyl-4,6-O-isopropylidene-1,2,3-tri-O-(methoxymethyl)-D-glycero-L-galactoheptitol

5,7-di-O-benzyl-4,6-O-isopropylidene-1,2,3-tri-O-methoxymethyl-D-glycero-L-ido-heptitol

5,7-di-O-benzyl-4,6-O-isopropylidene-D-glycero-L-ido-heptitol