(1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N³-benzyl-N¹-cyclopropyl-(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-cyclopropyl-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate
• CAS No.: 696628-82-7
• Molecular Formula: C₂₇H₃₈N₂O₈
• Molecular Weight: 518.607

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

Chemical Property:

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

There total 3 articles about (1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N³-benzyl-N¹-cyclopropyl-(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-cyclopropyl-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate (696628-82-7)

Guidance literature:

Multi-step reaction with 3 steps

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

2: ethanol / 16 h / 30 °C

3: 95 percent / CH₂Cl₂ / 4 h / 25 °C

With lithium hydroxide; In tetrahydrofuran; 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-cyclopropyl-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate (696628-82-7)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: ethanol / 16 h / 30 °C

4: 95 percent / CH₂Cl₂ / 4 h / 25 °C

With lithium hydroxide; 4 A molecular sieve; pyridinium chlorochromate; 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-cyclopropyl-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate (696628-82-7)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol / 16 h / 30 °C

2: 95 percent / CH₂Cl₂ / 4 h / 25 °C

In 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

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