1,6-Anhydro-3-O,4-O-isopropylidene-β-D-lyxo-2-hexosulopyranose

Base Information

• Chemical Name: 1,6-Anhydro-3-O,4-O-isopropylidene-β-D-lyxo-2-hexosulopyranose
• CAS No.: 17073-94-8
• Molecular Weight: 200.19
• Mol file: 17073-94-8.mol

Synonyms:1,6-Anhydro-3-O,4-O-isopropylidene-β-D-lyxo-2-hexosulopyranose

Chemical Property of 1,6-Anhydro-3-O,4-O-isopropylidene-β-D-lyxo-2-hexosulopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-Anhydro-3-O,4-O-isopropylidene-β-D-lyxo-2-hexosulopyranose

There total 5 articles about 1,6-Anhydro-3-O,4-O-isopropylidene-β-D-lyxo-2-hexosulopyranose 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: 63.0%

1,6-anhydro-3,4-O-isopropylidene-β-D-galactopyranose (52579-97-2) → 1,6-anhydro-3,4-O-isopropylidene-β-D-lyxo-hexopyranos-2-ulose (17073-94-8)

Guidance literature:

With pyridine; chromium(VI) oxide; acetic anhydride; In 1,2-dichloro-ethane; at 0 ℃; for 3h;

Reference yield:

1,6-anhydro-β-D-galactopyranose (644-76-8) → 1,6-anhydro-3,4-O-isopropylidene-β-D-lyxo-hexopyranos-2-ulose (17073-94-8)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH

2: (COCl)2, DMSO / tetrahydrofuran / -60 - -20 °C

With oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran;

DOI:10.1039/c39930001839

Reference yield:

acetone (67-64-1) + 1,6-Anhydro-2,3,4-tri-O-benzoyl-β-D-galactopyranose (91876-33-4) → 1,6-anhydro-3,4-O-isopropylidene-β-D-lyxo-hexopyranos-2-ulose (17073-94-8)

Guidance literature:

With ruthenium tetroxide; sodium methylate; hydrogen cation; Multistep reaction; 1.) MeOH;

DOI:10.1139/v87-191

upstream raw materials:

1,6-anhydro-3,4-O-isopropylidene-β-D-galactopyranose

acetone

1,6-Anhydro-2,3,4-tri-O-benzoyl-β-D-galactopyranose

1,6-anhydro-β-D-galactopyranose

Downstream raw materials:

(1R,2S,6S,7S,8R)-7-Benzyloxy-2-furan-3-yl-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane

3-((1R,2S,6S,7S,8R)-7-Benzyloxy-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undec-2-yl)-5H-furan-2-one

1,6-anhydro-3,4-O-isopropylidene-β-D-galactopyranose

Refernces

• 1、 Ohrui,Nishida,Higuchi,et al.. "The preferred rotamer about the C5-C6 bond of D-galactopyranoses and the stereochemistry of dehydrogenation by D-galactose oxidase". . p. 1145 - 1153. Retrieved 2007/10/02.