benzyl 2-(benzyloxycarbonylamino)-2-deoxy-5,6-O-isopropylidene-3-O--β-D-glucofuranoside

Base Information

• Chemical Name: benzyl 2-(benzyloxycarbonylamino)-2-deoxy-5,6-O-isopropylidene-3-O--β-D-glucofuranoside
• CAS No.: 80134-60-7
• Molecular Formula: C₂₈H₃₅NO₉
• Molecular Weight: 529.587
• Mol file: 80134-60-7.mol

Synonyms:benzyl 2-(benzyloxycarbonylamino)-2-deoxy-5,6-O-isopropylidene-3-O--β-D-glucofuranoside

Chemical Property of benzyl 2-(benzyloxycarbonylamino)-2-deoxy-5,6-O-isopropylidene-3-O--β-D-glucofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-(benzyloxycarbonylamino)-2-deoxy-5,6-O-isopropylidene-3-O--β-D-glucofuranoside

There total 1 articles about benzyl 2-(benzyloxycarbonylamino)-2-deoxy-5,6-O-isopropylidene-3-O--β-D-glucofuranoside 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: 89.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + benzyl 2-(benzyloxycarbonyl)amino-3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside (74072-31-4) → benzyl 2-(benzyloxycarbonylamino)-2-deoxy-5,6-O-isopropylidene-3-O--β-D-glucofuranoside (80134-60-7)

Guidance literature:

In diethyl ether; for 1h; Ambient temperature;

DOI:10.1016/S0008-6215(00)80687-4

Reference yield: 86.0%

benzyl 2-(benzyloxycarbonylamino)-2-deoxy-5,6-O-isopropylidene-3-O--β-D-glucofuranoside (80134-60-7) → benzyl 2-(benzyloxycarbonylamino)-2-deoxy-3-O--β-D-glucofuranoside (81148-68-7)

Guidance literature:

With acetic acid; In water; at 45 ℃; for 2h; Heating;

DOI:10.1016/S0008-6215(00)80687-4

Reference yield:

benzyl 2-(benzyloxycarbonylamino)-2-deoxy-5,6-O-isopropylidene-3-O--β-D-glucofuranoside (80134-60-7) → (R)-2-{(2R,3R,4R,5R)-4-Amino-5-benzyloxy-2-[(R)-2-hexadecanoylamino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-tetrahydro-furan-3-yloxy}-propionic acid methyl ester (82816-65-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / 60 percent acetic acid / H₂O / 2 h / 45 °C / Heating

2: 89 percent / pyridine / 5 h / -10 °C

3: 96 percent / 1.) p-toluenesulfonic acid monohydrate; 2.) Amberlite IR-45 (OH^-) ion-exchange resin / dioxane / 3 h / Ambient temperature

4: 87 percent / sodium azide / dimethylformamide / 15 h / 80 °C / Heating

5: Raney Ni (W-1) / ethanol / 1.5 h / Ambient temperature

6: dioxane / 5 h / Ambient temperature

7: hydrogen / 10 percent Pd-C / ethanol / 1 h / Ambient temperature

With pyridine; sodium azide; Amberlite IR-45 (OH^-) ion-exchange resin; hydrogen; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; Raney Ni (W-1); In 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)80687-4

upstream raw materials:

diazomethane

benzyl 2-(benzyloxycarbonyl)amino-3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside

Downstream raw materials:

benzyl 2-(benzyloxycarbonylamino)-2-deoxy-3-O--β-D-glucofuranoside

(R)-2-{(2R,3R,4R,5R)-4-Amino-5-benzyloxy-2-[(R)-2-octanoylamino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-tetrahydro-furan-3-yloxy}-propionic acid methyl ester

(R)-2-{(2R,3R,4R,5R)-2-[(R)-2-Amino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-5-benzyloxy-4-benzyloxycarbonylamino-tetrahydro-furan-3-yloxy}-propionic acid methyl ester

benzyl 2-(benzyloxycarbonylamino)-2-deoxy-6-O-mesyl-3-O--β-D-glucofuranoside