benzyl 2-(benzyloxycarbonylamino)-2,6-dideoxy-6-(hexadecanoylamino)-3-O--5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

Base Information

• Chemical Name: benzyl 2-(benzyloxycarbonylamino)-2,6-dideoxy-6-(hexadecanoylamino)-3-O--5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside
• CAS No.: 82816-53-3
• Molecular Formula: C₄₆H₇₀N₂O₁₀
• Molecular Weight: 811.069

Synonyms:

Chemical Property of benzyl 2-(benzyloxycarbonylamino)-2,6-dideoxy-6-(hexadecanoylamino)-3-O--5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-(benzyloxycarbonylamino)-2,6-dideoxy-6-(hexadecanoylamino)-3-O--5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

There total 6 articles about benzyl 2-(benzyloxycarbonylamino)-2,6-dideoxy-6-(hexadecanoylamino)-3-O--5-O-(tetrahydropyran-2-yl)-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:

benzyl 2-(benzyloxycarbonylamino)-2-deoxy-3-O--β-D-glucofuranoside (81148-68-7) → benzyl 2-(benzyloxycarbonylamino)-2,6-dideoxy-6-(hexadecanoylamino)-3-O--5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside (82816-53-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / pyridine / 5 h / -10 °C

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

3: 87 percent / sodium azide / dimethylformamide / 15 h / 80 °C / Heating

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

5: dioxane / 5 h / Ambient temperature

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

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) → benzyl 2-(benzyloxycarbonylamino)-2,6-dideoxy-6-(hexadecanoylamino)-3-O--5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside (82816-53-3)

Guidance literature:

Multi-step reaction with 6 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

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

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

Reference yield:

benzyl 2-(benzyloxycarbonylamino)-2-deoxy-6-O-mesyl-3-O--β-D-glucofuranoside (81148-76-7) → benzyl 2-(benzyloxycarbonylamino)-2,6-dideoxy-6-(hexadecanoylamino)-3-O--5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside (82816-53-3)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 87 percent / sodium azide / dimethylformamide / 15 h / 80 °C / Heating

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

4: dioxane / 5 h / Ambient temperature

With sodium azide; Amberlite IR-45 (OH^-) ion-exchange resin; toluene-4-sulfonic acid; Raney Ni (W-1); In 1,4-dioxane; ethanol; N,N-dimethyl-formamide;

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

upstream raw materials:

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

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

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

benzyl 6-azido-2-(benzyloxycarbonylamino)-2,6-dideoxy-3-O--5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

Downstream raw materials:

(R)-2-{(2R,3R,4R,5R)-5-Benzyloxy-4-hexadecanoylamino-2-[(R)-2-hexadecanoylamino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-tetrahydro-furan-3-yloxy}-propionic acid

benzyl 2,6-dideoxy-2,6-di(hexadecanoylamino)-3-O--5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

(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

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