(2S,3S)-1,2,3,4-Butanetetrol tetraacetate

Base Information

• Chemical Name: (2S,3S)-1,2,3,4-Butanetetrol tetraacetate
• CAS No.: 49560-29-4
• Molecular Formula: C₁₂H₁₈O₈
• Molecular Weight: 290.27
• Mol file: 49560-29-4.mol

Synonyms:(2S,3S)-1,2,3,4-Butanetetrol tetraacetate

Chemical Property of (2S,3S)-1,2,3,4-Butanetetrol tetraacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-1,2,3,4-Butanetetrol tetraacetate

There total 13 articles about (2S,3S)-1,2,3,4-Butanetetrol tetraacetate 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: 98.0%

D-threitol (2418-52-2,10030-58-7,188346-77-2,149-32-6) + acetic anhydride (108-24-7) → (D)-threitol tetraacetate (7208-40-4,49560-29-4,65167-69-3,73977-54-5,108392-14-9,102779-61-3)

Guidance literature:

With pyridine; dmap; for 5h; Inert atmosphere;

DOI:10.1039/c0cc00613k

Reference yield: 54.0%

rac-threitol (6968-16-7,10030-58-7,188346-77-2,149-32-6) + acetic anhydride (108-24-7) + benzyl bromide (100-39-0) → 2R,3R-tetritol tetraacetate (7208-40-4,49560-29-4,65167-69-3,73977-54-5,102779-61-3,108392-14-9) + 2,3,4-tri-O-acetyl-1-O-benzyl-D,L-threitol + 2,4-di-O-acetyl-1,3-di-O-benzyl-D,L-threitol

Guidance literature:

rac-threitol; With bis(tri-n-butyltin)oxide; In toluene; for 5h; Heating;

benzyl bromide; at 80 ℃; for 5h;

acetic anhydride; With pyridine; at 20 ℃;

DOI:10.1081/CAR-100106930

Reference yield: 50.0%

meso-erythritol (909878-64-4,10030-58-7,188346-77-2,149-32-6) + acetic anhydride (108-24-7) + benzyl bromide (100-39-0) → (D)-threitol tetraacetate (7208-40-4,49560-29-4,65167-69-3,73977-54-5,108392-14-9,102779-61-3) + 2,3,4-tri-O-acetyl-1-O-benzyl-D,L-erythritol + 2,4-di-O-acetyl-1,3-di-O-benzyl-D,L-erythritol

Guidance literature:

meso-erythritol; With bis(tri-n-butyltin)oxide; In toluene; for 5h; Heating;

benzyl bromide; at 80 ℃; for 20h;

acetic anhydride; With pyridine; at 20 ℃;

DOI:10.1081/CAR-100106930

upstream raw materials:

acetic acid

Glycolaldehyde

1,2,3,4-butanetetrol

acetic anhydride

Refernces

• 1、 Burroughs, Laurence,Vale, Matthew E.,Gilks, James A. R.,Forintos, Henrietta,Hayes, Christopher J.,Clarke, Paul A.. "Efficient asymmetric organocatalytic formation of erythrose and threose under aqueous conditions". supporting information; experimental part. p. 4776 - 4778. Retrieved 2010/09/05.
• 2、 Halila, Sami,Benazza, Mohammed,Demailly, Gilles. "Regioselective benzylation of pentitols, tetritols, and some hexitols via their stannyl ether derivatives: Versatile synthesis of monobenzylalditols". . p. 467 - 483. Retrieved 2007/10/03.