(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

Base Information

• Chemical Name: (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
• CAS No.: 82816-64-6
• Molecular Formula: C₃₀H₄₈N₂O₈
• Molecular Weight: 564.72
• Mol file: 82816-64-6.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 8 articles about (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 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)-2,6-dideoxy-3-O--6-(octanoylamino)-5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside (81148-69-8) → (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 (82816-64-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 1h; Ambient temperature;

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

Reference yield:

benzyl 2-(benzyloxycarbonylamino)-2-deoxy-3-O--β-D-glucofuranoside (81148-68-7) → (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 (82816-64-6)

Guidance literature:

Multi-step reaction with 6 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

6: 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; palladium on activated charcoal; 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) → (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 (82816-64-6)

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:

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

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

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

(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

Downstream raw materials:

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

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

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

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