(E)-N,N-diethyl-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranosiduronamide

Base Information

• Chemical Name: (E)-N,N-diethyl-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranosiduronamide
• CAS No.: 1310802-56-2
• Molecular Formula: C₂₁H₂₉NO₅
• Molecular Weight: 375.465
• Mol file: 1310802-56-2.mol

Synonyms:(E)-N,N-diethyl-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranosiduronamide

Chemical Property of (E)-N,N-diethyl-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranosiduronamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-N,N-diethyl-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranosiduronamide

There total 3 articles about (E)-N,N-diethyl-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranosiduronamide 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: 67.0%

N,N-diethyldichloroacetamide (921-88-0) + 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → (E)-N,N-diethyl-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranosiduronamide (1310802-56-2)

Guidance literature:

With chromium dichloride; In tetrahydrofuran; at 75 ℃; for 3h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1021/jo200548g

Reference yield: 26.0%

dimethyl (2-(diethylamino)-2-oxoethyl)phosphonate (104584-00-1) + 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → (E)-N,N-diethyl-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranosiduronamide (1310802-56-2) + (Z)-N,N-diethyl-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranosiduronamide (1450618-18-4)

Guidance literature:

dimethyl (2-(diethylamino)-2-oxoethyl)phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h; Inert atmosphere;

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Overall yield = 66 %; Inert atmosphere;

DOI:10.1002/ejoc.201300322

Reference yield:

2-bromo-N,N-diethylacetamide (2430-01-5) → (E)-N,N-diethyl-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranosiduronamide (1310802-56-2) + (Z)-N,N-diethyl-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranosiduronamide (1450618-18-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ethyl acetate / 72 h / Reflux

2.1: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 °C / Inert atmosphere

With n-butyllithium; In tetrahydrofuran; hexane; ethyl acetate; 2.1: |Horner-Wadsworth-Emmons Olefination / 2.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1002/ejoc.201300322

upstream raw materials:

N,N-diethyldichloroacetamide

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

2-bromo-N,N-diethylacetamide

dimethyl (2-(diethylamino)-2-oxoethyl)phosphonate

Downstream raw materials:

2-chloro-N,N-diethyl-3-[(4R)-3-O-benzyl-1,2-O-isopropylidene-β-L-threofuran-4-yl]cyclopropanecarboxamide