1,6-ANHYDRO-2,3-DIDEOXY-BETA-D-THREO-HEX-2-ENOPYRANOSE

Base Information

• Chemical Name: 1,6-ANHYDRO-2,3-DIDEOXY-BETA-D-THREO-HEX-2-ENOPYRANOSE
• CAS No.: 58394-32-4
• Molecular Formula: C6H8O3
• Molecular Weight: 128.128
• Mol file: 58394-32-4.mol

Synonyms:1,6-ANHYDRO-2,3-DIDEOXY-BETA-D-THREO-HEX-2-ENOPYRANOSE;1,6-Anhydro-2,3-dideoxy-b-D-threo-hex-2-enopyranose

Chemical Property of 1,6-ANHYDRO-2,3-DIDEOXY-BETA-D-THREO-HEX-2-ENOPYRANOSE

Chemical Property:

• Boiling Point: 264.5±40.0 °C(Predicted)
• PKA: 13.73±0.20(Predicted)
• PSA: 38.69000
• Density: 1.344±0.06 g/cm3(Predicted)
• LogP: -0.34140

Purity/Quality:

97% ^*data from raw suppliers

1,6-Anhydro-2,3-dideoxy-b-D-threo-hex-2-enopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,6-ANHYDRO-2,3-DIDEOXY-BETA-D-THREO-HEX-2-ENOPYRANOSE

There total 23 articles about 1,6-ANHYDRO-2,3-DIDEOXY-BETA-D-THREO-HEX-2-ENOPYRANOSE 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: 92.0%

(-)-(1R,4R,5R)-7,8-Dioxabicyclo[3.2.1]oct-3-en-2-yl acetate (33648-08-7) → 1,6-anhydro-2,3-dideoxy-β-threo-hex-2-enopyranose (58394-32-4,52630-80-5,52630-81-6)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 0.166667h;

DOI:10.1055/s-2000-7099

Reference yield: 57.0%

C6H6O4 (58238-41-8) → 1,6-anhydro-2,3-dideoxy-β-threo-hex-2-enopyranose (58394-32-4,52630-80-5,52630-81-6)

Guidance literature:

C₆H₆O₄; With hydrazine; In tetrahydrofuran; methanol; at 18 ℃; for 1h;

With acetic acid; In tetrahydrofuran; methanol; at 18 ℃; for 1h;

DOI:10.1071/CH14574

Reference yield: 51.0%

(+/-)-7,8-Dioxabicyclo[3.2.1]oct-3-en-2-yl acetate → 1,6-anhydro-2,3-dideoxy-β-threo-hex-2-enopyranose (58394-32-4,52630-80-5,52630-81-6) + 1,6-anhydro-4-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranose (307991-10-2)

Guidance literature:

With Lipase AK immobilized on Celite; Pseudomonas sp. Amano; In phosphate buffer; acetone; at 20 ℃; for 24h; pH=7.2; Enzymatic reaction;

DOI:10.1055/s-2000-7099

upstream raw materials:

D-galactal

(-)-(1R,4R,5R)-7,8-Dioxabicyclo[3.2.1]oct-3-en-2-yl acetate

isolevoglucosenone

1,6-anhydro-2,3-dideoxy-β-D-erythro-hex-2-enopyranose

Downstream raw materials:

isolevoglucosenone

1,6-anhydro-4-O-p-methoxybenzyl-2,3-dideoxy-β-D-threo-hex-2-enopyranose

1,6:2,3-dianhydro-2,3-epithio-4-O-p-methoxybenzyl-β-D-talopyranose

1,6-anhydro-4-O-p-methoxybenzyl-β-D-gulopyranose

Refernces

• 1、 Ma, Xinghua,Anderson, Natasha,White, Lorenzo V.,Bae, Song,Raverty, Warwick,Willis, Anthony C.,Banwell, Martin G.. "The conversion of levoglucosenone into isolevoglucosenone". . p. 593 - 599. Retrieved 2015/04/27.
• 2、 Kadota,ElAzab,Taniguchi,Ogasawara. "Lipase-mediated preparation of enantiopure isolevoglucosenone". . p. 1372 - 1374. Retrieved 2007/10/03.