(Z)-2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucono hydroximo-1,5-lactone

Base Information

• Chemical Name: (Z)-2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucono hydroximo-1,5-lactone
• CAS No.: 201736-68-7
• Molecular Formula: C₆₁H₆₃NO₁₁
• Molecular Weight: 986.171
• Mol file: 201736-68-7.mol

Synonyms:(Z)-2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucono hydroximo-1,5-lactone

Chemical Property of (Z)-2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucono hydroximo-1,5-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucono hydroximo-1,5-lactone

There total 1 articles about (Z)-2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucono hydroximo-1,5-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: 62.0%

2,3,6-tris-O-(phenylmethyl)-4-O-[2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-glucopyranosyl]-D-glucopyranoside (148968-90-5) → (Z)-2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucono hydroximo-1,5-lactone (201736-68-7)

Guidance literature:

2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucopyranose; With hydroxylamine hydrochloride; sodium methylate; In methanol; for 1.5h; Heating;

With N-chloro-succinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -78 ℃; for 0.2h; Further stages.;

DOI:10.1021/ja012659q

Reference yield:

(Z)-2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucono hydroximo-1,5-lactone (201736-68-7) → 1,5-anhydro-1-azi-2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucitol (201736-74-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / triethylamine / CH₂Cl₂ / 0.33 h / 0 °C

2: 81 percent / methanolic ammonia / CH₂Cl₂ / 50 h / 25 °C

3: 95 percent / I₂; trimethylamine / CH₂Cl₂ / 1.5 h / -78 °C

With ammonia; iodine; triethylamine; trimethylamine; In dichloromethane;

DOI:10.1021/ja012659q

Reference yield:

(Z)-2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucono hydroximo-1,5-lactone (201736-68-7) → 1,5-anhydro-2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-hydrazi-D-glucitol (201736-72-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / triethylamine / CH₂Cl₂ / 0.33 h / 0 °C

2: 81 percent / methanolic ammonia / CH₂Cl₂ / 50 h / 25 °C

With ammonia; triethylamine; In dichloromethane;

DOI:10.1021/ja012659q

upstream raw materials:

2,3,6-tris-O-(phenylmethyl)-4-O-[2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-glucopyranosyl]-D-glucopyranoside

Downstream raw materials:

1,5-anhydro-1-azi-2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucitol

1,5-anhydro-2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-hydrazi-D-glucitol