(1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N³-(4-chlorophenyl)-N¹-benzyl-(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-(4-chlorophenyl)-N¹-benzyl-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate
• CAS No.: 696629-05-7
• Molecular Formula: C₃₀H₃₇ClN₂O₈
• Molecular Weight: 589.085

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

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

There total 6 articles about (1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N³-(4-chlorophenyl)-N¹-benzyl-(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: 98.0%

p-chlorphenylisocyanate (104-12-1) + ethyl 6-benzylamino-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-octopyranuronate (437552-42-6) → (1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N3-(4-chlorophenyl)-N1-benzyl-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate (696629-05-7)

Guidance literature:

In dichloromethane; at 25 ℃; for 4h;

DOI:10.1081/CAR-120030140

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-(4-chlorophenyl)-N1-benzyl-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate (696629-05-7)

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 / 4 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-(4-chlorophenyl)-N1-benzyl-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate (696629-05-7)

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 / 4 h / 25 °C

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

DOI:10.1081/CAR-120030140

upstream raw materials:

p-chlorphenylisocyanate

ethyl 6-benzylamino-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-octopyranuronate

(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

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