3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
• CAS No.: 125946-65-8
• Molecular Formula: C₃₇H₃₃Cl₃N₂O₇
• Molecular Weight: 724.037
• Mol file: 125946-65-8.mol

Synonyms:3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

Chemical Property of 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

There total 8 articles about 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 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: 92.0%

2-((3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-3-yl)-isoindole-1,3-dione (125946-77-2) + trichloroacetonitrile (545-06-2) → 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate (125946-65-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,2-dichloro-ethane; at 20 ℃; for 16h;

DOI:10.1016/0008-6215(90)84222-G

Reference yield:

2-((2R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione (89067-86-7) → 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate (125946-65-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Ag₂O-KI-BnBr / dimethylformamide

2: 1. PdCl₂-AcONa 2. Cl₃CCN-DBU / solvents: 1. aq. AcOH 2. (CH₂Cl₂)

With sodium acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trichloroacetonitrile; palladium dichloride; silver(l) oxide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)99376-6

Reference yield:

benzyl bromide (100-39-0) → 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate (125946-65-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / Ag₂O, KI / dimethylformamide / 1 h / 5 °C

2: 82 percent / 95percent HOAc, AcONa, PdCl₂ / 20 h / 20 °C

3: 92 percent / DBU / 1,2-dichloro-ethane / 16 h / 20 °C

With sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium iodide; palladium dichloride; silver(l) oxide; In 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(90)84222-G

upstream raw materials:

2-((2R,4R,5S,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

2-((3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

trichloroacetonitrile

2-((2R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

Downstream raw materials:

allyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-O-(3,6-di-O-allyl-2-O-benzyl-β-D-mannopyranosyl)-(1->4)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3-O-benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phtha...