2,5-anhydro-1,4-dideoxy-D-xylo-hexitol

Base Information

• Chemical Name: 2,5-anhydro-1,4-dideoxy-D-xylo-hexitol
• CAS No.: 82109-99-7
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.159
• Mol file: 82109-99-7.mol

Synonyms:

Chemical Property of 2,5-anhydro-1,4-dideoxy-D-xylo-hexitol

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-anhydro-1,4-dideoxy-D-xylo-hexitol

There total 46 articles about 2,5-anhydro-1,4-dideoxy-D-xylo-hexitol 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: 97.0%

C13H18O3 (949932-83-6) → (2S,3S,5S)-5-hydroxymethyl-2-methyltetrahydrofuran-3-ol (82109-99-7)

Guidance literature:

nickel; In methanol; at 20 ℃; for 1h;

DOI:10.1021/ol071176+

Reference yield: 97.0%

2,5-anhydro-3-O-benzoyl-1,4-dideoxy-D-xylo-hexitol (111967-30-7) → (2S,3S,5S)-5-hydroxymethyl-2-methyltetrahydrofuran-3-ol (82109-99-7)

Guidance literature:

sodium methylate; In methanol;

Reference yield: 88.0%

(2S,3S,5S)-5-[(dimethylbenzhydrylsilyl)methyl]-2-methyl-tetrahydrofuran-3-ol → (2S,3S,5S)-5-hydroxymethyl-2-methyltetrahydrofuran-3-ol (82109-99-7)

Guidance literature:

With tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hydrogencarbonate; In methanol; for 13h;

DOI:10.1021/ja012193b

upstream raw materials:

(4S,5S)-2,2,4-Trimethyl-5-(R)-1-oxiranylmethyl-[1,3]dioxolane

anhydro-1,4-dideoxy-D-gluco-heptitol

2,5-anhydro-3-O-benzoyl-1,4-dideoxy-D-xylo-hexitol

Benzoic acid (2S,4S,5S)-4-hydroxy-5-methyl-tetrahydro-furan-2-ylmethyl ester

Downstream raw materials:

L-(+)-epimuscarine toluene-p-sulphonate

2,5-anhydro-1,4-dideoxy-6-O-(p-tolylsulphonyl)-D-xylo-hexitol

Refernces

• 1、 Angle, Steven R.,El-Said, Nahla A.. "Stereoselective synthesis of tetrahydrofurans via formal [3+2]-cycloaddition of aldehydes and allylsilanes. Formal total synthesis of the muscarine alkaloids (-)-allomuscarine and (+)-epimuscarine". . p. 3608 - 3613. Retrieved 2007/10/03.
• 2、 Adams,Poupart,Grenier. "Diastereoselectivity in the synthesis of 3(2H)-furanones. Total synthesis of (+)-muscarine". . p. 1753 - 1756. Retrieved 2007/10/02.