1,5-anhydro-3-azido-4,6-O-benzylidene-2,3-dideoxy-D-arabino-hex-1-enitol

Base Information

• Chemical Name: 1,5-anhydro-3-azido-4,6-O-benzylidene-2,3-dideoxy-D-arabino-hex-1-enitol
• CAS No.: 74644-56-7
• Molecular Formula: C₁₃H₁₃N₃O₃
• Molecular Weight: 259.265
• Mol file: 74644-56-7.mol

Synonyms:1,5-anhydro-3-azido-4,6-O-benzylidene-2,3-dideoxy-D-arabino-hex-1-enitol

Chemical Property of 1,5-anhydro-3-azido-4,6-O-benzylidene-2,3-dideoxy-D-arabino-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5-anhydro-3-azido-4,6-O-benzylidene-2,3-dideoxy-D-arabino-hex-1-enitol

There total 9 articles about 1,5-anhydro-3-azido-4,6-O-benzylidene-2,3-dideoxy-D-arabino-hex-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: 15.0%

3-O-acetyl-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enitol (72074-91-0) → 1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose (63598-38-9,167074-37-5) + 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl azide + 1,5-anhydro-3-azido-4,6-O-benzylidene-2,3-dideoxy-D-arabino-hex-1-enitol (74644-56-7) + 3-azido-4,6-O-benzylidene-3-deoxy-D-allal

Guidance literature:

With sodium azide; sodium; boron trifluoride diethyl etherate; Yield given. Multistep reaction. Yields of byproduct given; 1.) room temp., acetonitrile, 2 h; 2.) methanol, room temp., 16 h;

DOI:10.1016/S0008-6215(00)85699-2

Reference yield:

1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose (63598-38-9,167074-37-5) → 1,5-anhydro-3-azido-4,6-O-benzylidene-2,3-dideoxy-D-arabino-hex-1-enitol (74644-56-7)

Guidance literature:

With diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 25 ℃;

DOI:10.1016/0040-4039(95)01575-3

Reference yield:

4,6-O-benzylidene-3-O-methyl-D-allal (16697-45-3) → (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine (65530-27-0) + 1,5-anhydro-3-azido-4,6-O-benzylidene-2,3-dideoxy-D-arabino-hex-1-enitol (74644-56-7) + 3-azido-4,6-O-benzylidene-3-deoxy-D-allal

Guidance literature:

With sodium azide; sodium; boron trifluoride diethyl etherate; Yield given. Multistep reaction; 1.) room temp., acetonitrile, 2 h; 2.) methanol, room temp., 16 h;

DOI:10.1016/S0008-6215(00)85699-2

upstream raw materials:

4,6-O-benzylidene-3-O-methyl-D-allal

(4aR,6R,8aS)-6-methoxy-2-(4-methoxyphenyl)-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine

3-O-acetyl-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enitol

(2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine

Downstream raw materials:

4,6-O-benzylidene-3-deoxy-3-isothiocyanato-D-glucal

3-acetamido-4,6-O-benzylidene-3-deoxy-D-glucal

(2R,4aR,8R,8aS)-2-Phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-ylamine

((2R,4aR,8R,8aS)-2-Phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yl)-carbamic acid benzyl ester