(1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N³-benzyl-N¹-(3,4-dimethoxyphenyl methyl)-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate

Base Information

• Chemical Name: (1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N³-benzyl-N¹-(3,4-dimethoxyphenyl methyl)-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate
• CAS No.: 696629-11-5
• Molecular Formula: C₃₃H₄₄N₂O₁₀
• Molecular Weight: 628.72

Synonyms:(1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N³-benzyl-N¹-(3,4-dimethoxyphenyl methyl)-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate

Chemical Property of (1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N³-benzyl-N¹-(3,4-dimethoxyphenyl methyl)-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N³-benzyl-N¹-(3,4-dimethoxyphenyl methyl)-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate

There total 5 articles about (1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N³-benzyl-N¹-(3,4-dimethoxyphenyl methyl)-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate 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:

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde (4933-77-1) → (1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N3-benzyl-N1-(3,4-dimethoxyphenyl methyl)-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate (696629-11-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / lithium hydroxide monohydrate / tetrahydrofuran / 10 h

2: ammonia / ethanol / 24 h / 30 °C

3: trimethyl orthoformate / CH₂Cl₂ / 4 h / 0 °C

4: sodium cyanoborohydride / CH₂Cl₂ / 12 h / 30 °C

5: 98 percent / CH₂Cl₂ / 3 h / 25 °C

With lithium hydroxide; ammonia; sodium cyanoborohydride; trimethyl orthoformate; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1081/CAR-120030140

Reference yield:

(E)-ethyl 6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-6-eno-octopyranuronate (71553-89-4) → (1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N3-benzyl-N1-(3,4-dimethoxyphenyl methyl)-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate (696629-11-5)

Guidance literature:

Multi-step reaction with 4 steps

1: ammonia / ethanol / 24 h / 30 °C

2: trimethyl orthoformate / CH₂Cl₂ / 4 h / 0 °C

3: sodium cyanoborohydride / CH₂Cl₂ / 12 h / 30 °C

4: 98 percent / CH₂Cl₂ / 3 h / 25 °C

With ammonia; sodium cyanoborohydride; trimethyl orthoformate; In ethanol; dichloromethane;

DOI:10.1081/CAR-120030140

Reference yield:

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → (1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N3-benzyl-N1-(3,4-dimethoxyphenyl methyl)-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate (696629-11-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 56.4 percent / pyridinium chlorochromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h

2: 85 percent / lithium hydroxide monohydrate / tetrahydrofuran / 10 h

3: ammonia / ethanol / 24 h / 30 °C

4: trimethyl orthoformate / CH₂Cl₂ / 4 h / 0 °C

5: sodium cyanoborohydride / CH₂Cl₂ / 12 h / 30 °C

6: 98 percent / CH₂Cl₂ / 3 h / 25 °C

With lithium hydroxide; 4 A molecular sieve; ammonia; sodium cyanoborohydride; pyridinium chlorochromate; trimethyl orthoformate; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1081/CAR-120030140

upstream raw materials:

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde

(E)-ethyl 6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-6-eno-octopyranuronate

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

ethyl (methyl 1,2:3,4-di-O-isopropylidene-6-amino-6,7-dideoxy-L-glycero-α-D-galacto-octopyranoside)uronate

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