6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose

Base Information

• Chemical Name: 6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose
• CAS No.: 76951-92-3
• Molecular Formula: C₂₁H₂₉NO₈
• Molecular Weight: 423.463
• Mol file: 76951-92-3.mol

Synonyms:6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose

Chemical Property of 6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose

There total 12 articles about 6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose 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: 82.0%

7-O-acetyl-6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose (83051-84-7) → 6-N,7-O-carbonyl-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose (83051-85-8) + 6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose (76951-92-3)

Guidance literature:

With sodium methylate; In methanol; for 1h; Ambient temperature;

DOI:10.1016/S0008-6215(00)82223-5

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) → 6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose (76951-92-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 2.) mesilating agent / 2.) pyridine

2: lithium aluminium hydride

3: benzyloxycarbonylating agent / H₂O; dioxane

5: deacetylative agent

With lithium aluminium tetrahydride; benzyloxycarbonylating agent; deacetylative agent; mesilating agent; In 1,4-dioxane; water;

DOI:10.1246/cl.1980.1439

Reference yield:

(R)-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-aziridine (76951-84-3,76951-90-1) → 6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose (76951-92-3)

Guidance literature:

Multi-step reaction with 3 steps

1: benzyloxycarbonylating agent / H₂O; dioxane

3: deacetylative agent

With benzyloxycarbonylating agent; deacetylative agent; In 1,4-dioxane; water;

DOI:10.1246/cl.1980.1439

upstream raw materials:

7-O-acetyl-6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose

(R)-2-Amino-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethanol

benzyl chloroformate

Benzyl-[(R)-2-hydroxy-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-carbamic acid benzyl ester

Downstream raw materials:

[(R)-2-Hydroxy-1-((2R,3R,4S,5R)-3,4,5-trihydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-carbamic acid benzyl ester