(R)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(2-benzyloxy-acetylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester

Base Information

• Chemical Name: (R)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(2-benzyloxy-acetylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester
• CAS No.: 76379-10-7
• Molecular Formula: C₄₁H₄₂N₂O₁₁
• Molecular Weight: 738.791

Synonyms:(R)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(2-benzyloxy-acetylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester

Chemical Property of (R)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(2-benzyloxy-acetylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (R)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(2-benzyloxy-acetylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester

There total 5 articles about (R)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(2-benzyloxy-acetylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl 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: 99.6%

N-hydroxy-5-norbornene-2,3-dicarboximide (21715-90-2) + benzyl 4,6-O-benzylidene-2-benzyloxyacetamido-3-O-<1-(R)-carboxyethyl>-2-deoxy-α-D-glucopyranoside (66111-70-4) → (R)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(2-benzyloxy-acetylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester (76379-10-7)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 4 - 20 ℃; for 19h;

DOI:10.1246/bcsj.53.2570

Reference yield:

benzyl 4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyranoside (13347-83-6) → (R)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(2-benzyloxy-acetylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester (76379-10-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / tetrahydrofuran / 1 h / Heating

2: 1.) NaH / 1.) dioxane, 90 deg C, 1 h, 2.) dioxane, 65 deg C, 16 h

3: 99.6 percent / dicyclohexylcarbodiimide (DCC) / tetrahydrofuran / 19 h / 4 - 20 °C

With sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1246/bcsj.53.2570

Reference yield:

benzyloxyacetic acid (30379-55-6) → (R)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(2-benzyloxy-acetylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester (76379-10-7)

Guidance literature:

Multi-step reaction with 4 steps

1: dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 17 h / 0 - 20 °C

2: 100 percent / tetrahydrofuran / 1 h / Heating

3: 1.) NaH / 1.) dioxane, 90 deg C, 1 h, 2.) dioxane, 65 deg C, 16 h

4: 99.6 percent / dicyclohexylcarbodiimide (DCC) / tetrahydrofuran / 19 h / 4 - 20 °C

With sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1246/bcsj.53.2570

upstream raw materials:

N-hydroxy-5-norbornene-2,3-dicarboximide

benzyl 4,6-O-benzylidene-2-benzyloxyacetamido-3-O-<1-(R)-carboxyethyl>-2-deoxy-α-D-glucopyranoside

benzyl 4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyranoside

benzyloxyacetic acid

Downstream raw materials:

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

(R)-4-((S)-2-{(R)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(2-benzyloxy-acetylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionylamino}-3-methyl-butyrylamino)-4-carbamoyl-butyric acid benzyl ester

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

(R)-4-((S)-2-{(R)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(2-benzyloxy-acetylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionylamino}-4-methyl-pentanoylamino)-4-carbamoyl-butyric acid benzyl ester

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