.beta.-D-Glucofuranosiduronic acid, methyl 2-(acetylamino)-2-deoxy-, .gamma.-lactone

Base Information

• Chemical Name: .beta.-D-Glucofuranosiduronic acid, methyl 2-(acetylamino)-2-deoxy-, .gamma.-lactone
• CAS No.: 153373-84-3
• Molecular Formula: C₉H₁₃NO₆
• Molecular Weight: 231.205
• Mol file: 153373-84-3.mol

Synonyms:Acetamide,N-(hexahydro-6-hydroxy-2-methoxy-5-oxofuro[3,2-b]furan-3-yl)-, [2R-(2a,3b,3ab,6a,6ab)]-; Furo[3,2-b]furan, acetamide deriv.

Chemical Property of .beta.-D-Glucofuranosiduronic acid, methyl 2-(acetylamino)-2-deoxy-, .gamma.-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of .beta.-D-Glucofuranosiduronic acid, methyl 2-(acetylamino)-2-deoxy-, .gamma.-lactone

There total 4 articles about .beta.-D-Glucofuranosiduronic acid, methyl 2-(acetylamino)-2-deoxy-, .gamma.-lactone 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:

methyl 2-acetamido-2-deoxy-β-D-glucofuranoside (5517-54-4) → methyl 2-acetamido-2-deoxy-β-D-xylo-hexofuranosid-5-ulose (153373-82-1) + methyl (methyl 2-acetamido-2-deoxy-β-D-glucofuranosid)uronate (153373-85-4) + methyl 2-acetamido-2-deoxy-β-D-glucofuranosidurono-6,3-lactone (153373-84-3)

Guidance literature:

With bromine; tributyltin methoxide; di(n-butyl)tin oxide; Yield given. Multistep reaction. Yields of byproduct given; 1.) methanol, -15 deg C, 2.) CH₂Cl₂;

DOI:10.1016/S0040-4020(01)80229-5

Reference yield:

methanol (67-56-1) + methyl 2-acetamido-2-deoxy-β-D-glucofuranoside (5517-54-4) → methyl 2-acetamido-2-deoxy-β-D-xylo-hexofuranosid-5-ulose (153373-82-1) + methyl (methyl 2-acetamido-2-deoxy-β-D-glucofuranosid)uronate (153373-85-4) + methyl 2-acetamido-2-deoxy-β-D-glucofuranosidurono-6,3-lactone (153373-84-3)

Guidance literature:

With bromine; tributyltin methoxide; di(n-butyl)tin oxide; Yield given. Multistep reaction. Yields of byproduct given; 1.) 0 deg C, 2.) CH₂Cl₂;

DOI:10.1016/S0040-4020(01)80229-5

Reference yield:

methyl 2-acetamido-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside (50605-03-3) → methyl 2-acetamido-2-deoxy-β-D-glucofuranosidurono-6,3-lactone (153373-84-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / acetic acid; H₂O / 5 h / Ambient temperature

2: 1.) dibutyltin oxide, 2.) Br₂, tributyltin methoxide / 1.) 0 deg C, 2.) CH₂Cl₂

With bromine; tributyltin methoxide; di(n-butyl)tin oxide; In water; acetic acid;

DOI:10.1016/S0040-4020(01)80229-5

upstream raw materials:

methanol

methyl 2-acetamido-2-deoxy-β-D-glucofuranoside

methyl 2-acetamido-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside

2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline

Refernces