N,N'-DIACETYL-3,6,3',4',6'-PENTA-O-ACETYL-1-CHLOROCHITOBIOSIDE

Base Information

• Chemical Name: N,N'-DIACETYL-3,6,3',4',6'-PENTA-O-ACETYL-1-CHLOROCHITOBIOSIDE
• CAS No.: 7531-49-9
• Molecular Formula: C26H37ClN2O15
• Molecular Weight: 653.02938
• Mol file: 7531-49-9.mol

Synonyms:N,N'-DIACETYL-3,6,3',4',6'-PENTA-O-ACETYL-1-CHLOROCHITOBIOSIDE;2-(AcetylaMino)-2-deoxy-4-O-[3,4,6-tri-O-acetyl-2-(acetylaMino)-2-deoxy-β-D-glucopyranosyl]-α-D-glucopyranosyl Chloride 3,6-Diacetate;2-AcetaMido-4-O-(2-acetaMido-2-deoxy-β-D-glucopyranosyl)-

Chemical Property of N,N'-DIACETYL-3,6,3',4',6'-PENTA-O-ACETYL-1-CHLOROCHITOBIOSIDE

Chemical Property:

• PSA: 224.37000
• LogP: 0.67150
• Solubility.: Chloroform

Purity/Quality:

97% ^*data from raw suppliers

[(3S,6S)-5-Acetamido-6-[(3S,6R)-5-acetamido-4-acetyloxy-2-(acetyloxymethyl)-6-chlorooxan-3-yl]oxy-3,4-diacetyloxyoxan-2-yl]methylacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N,N’-Diacetyl-3,6,3’,4’,6’-penta-O-acetyl-1-chlorochitobioside (cas# 7531-49-9) is a compound useful in organic synthesis.

Technology Process of N,N'-DIACETYL-3,6,3',4',6'-PENTA-O-ACETYL-1-CHLOROCHITOBIOSIDE

There total 2 articles about N,N'-DIACETYL-3,6,3',4',6'-PENTA-O-ACETYL-1-CHLOROCHITOBIOSIDE 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: 88.0%

chitobiose octaacetate (7284-18-6) → 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride (7531-49-9)

Guidance literature:

With hydrogenchloride;

Reference yield:

2-amino-2-deoxy-β-D-glucopyranosyl-(1->4)-2-amino-2-deoxy-D-glucopyranose (77224-08-9) + acetyl chloride (75-36-5) → 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride (7531-49-9)

Guidance literature:

Reference yield:

2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride (7531-49-9) → N4-<2-Acetamido-4-O-(2-acetamido-2-desoxy-β-D-glucopyranosyl)-2-desoxy-β-D-glucopyranosyl>-N2-(tert-butyloxycarbonyl)-L-asparaginyl-L-phenylalanyl-L-treoninamid (98304-20-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / sodium azide, tricaprylmethylammonium chloride / H₂O; CHCl₃ / Ambient temperature

2: 60 percent / H₂ / PtO₂

3: 91 percent / EEDQ / CH₂Cl₂ / 72 h / Ambient temperature

4: 95 percent / morpholine / (Ph₃P)4Pd⁽⁰⁾ / tetrahydrofuran; dimethylsulfoxide / 4 h / Ambient temperature

5: 81 percent / triethylamine, EEDQ / dimethylformamide / 72 h / Ambient temperature

6: 86 percent / NH₃ / methanol / 48 h / Ambient temperature

With morpholine; sodium azide; ammonia; hydrogen; Aliquat 336; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; platinum(IV) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

chitobiose octaacetate

2-amino-2-deoxy-β-D-glucopyranosyl-(1->4)-2-amino-2-deoxy-D-glucopyranose

acetyl chloride

Downstream raw materials:

dibenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucopyranosyl phosphate

N⁴-<2-Acetamido-4-O-(2-acetamido-2-desoxy-β-D-glucopyranosyl)-2-desoxy-β-D-glucopyranosyl>-N²-(tert-butyloxycarbonyl)-L-asparaginyl-L-phenylalanyl-L-treoninamid

N⁴-<2-Acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-desoxy-β-D-glucopyranosyl>-N²-(tert-butyloxycarbonyl)-L-asparaginyl-L-phenylalanyl-L-threonin-allylester

N⁴-<2-Acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-desoxy-β-D-glucopyranosyl>-L-asparaginyl-L-phenylalanyl-L-treonin-allylester-trifluoracetat