(R)-4-((S)-2-{(S)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(3-hydroxy-tetradecanoylamino)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid benzyl ester

Base Information

• Chemical Name: (R)-4-((S)-2-{(S)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(3-hydroxy-tetradecanoylamino)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid benzyl ester
• CAS No.: 78397-89-4
• Molecular Formula: C₄₈H₇₂N₄O₁₂
• Molecular Weight: 897.119
• Mol file: 78397-89-4.mol

Synonyms:

Chemical Property of (R)-4-((S)-2-{(S)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(3-hydroxy-tetradecanoylamino)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-((S)-2-{(S)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(3-hydroxy-tetradecanoylamino)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid benzyl ester

There total 9 articles about (R)-4-((S)-2-{(S)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(3-hydroxy-tetradecanoylamino)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid benzyl 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:

N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide (66026-10-6) → (R)-4-((S)-2-{(S)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(3-hydroxy-tetradecanoylamino)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid benzyl ester (78397-89-4)

Guidance literature:

Multi-step reaction with 9 steps

1: hydrazine hydrate / Heating

2: by (benzyloxycarbonyl)ation

3: sodium hydride

5: H₂ / 10percent palladium-carbon / methanol / 0.5 h

7: sodium borohydride / methanol / 0 °C

8: 0.1 M aq. potassium hydroxide / dioxane

9: dicyclohexylcarbodiimide/N-hydroxysuccinimide

With potassium hydroxide; sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; sodium hydride; hydrazine hydrate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol;

DOI:10.1016/S0008-6215(00)85936-4

Reference yield:

benzyl 2-(benzyloxycarbonylamino)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside (77277-23-7) → (R)-4-((S)-2-{(S)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(3-hydroxy-tetradecanoylamino)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid benzyl ester (78397-89-4)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium hydride

3: H₂ / 10percent palladium-carbon / methanol / 0.5 h

5: sodium borohydride / methanol / 0 °C

6: 0.1 M aq. potassium hydroxide / dioxane

7: dicyclohexylcarbodiimide/N-hydroxysuccinimide

With potassium hydroxide; sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; sodium hydride; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol;

DOI:10.1016/S0008-6215(00)85936-4

Reference yield:

O-phenylmethyl 2-amino-2-deoxy-4,6-O-(1-methylethylidene)-α-D-glucopyranoside (66026-11-7) → (R)-4-((S)-2-{(S)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(3-hydroxy-tetradecanoylamino)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid benzyl ester (78397-89-4)

Guidance literature:

Multi-step reaction with 8 steps

1: by (benzyloxycarbonyl)ation

2: sodium hydride

4: H₂ / 10percent palladium-carbon / methanol / 0.5 h

6: sodium borohydride / methanol / 0 °C

7: 0.1 M aq. potassium hydroxide / dioxane

8: dicyclohexylcarbodiimide/N-hydroxysuccinimide

With potassium hydroxide; sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; sodium hydride; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol;

DOI:10.1016/S0008-6215(00)85936-4

upstream raw materials:

L-alanyl-(γ-benzyl ester D-isoglutamine)

N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide

benzyl 2-(benzyloxycarbonylamino)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

O-phenylmethyl 2-amino-2-deoxy-4,6-O-(1-methylethylidene)-α-D-glucopyranoside

Refernces