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

Base Information

• Chemical Name: 7-O-acetyl-6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose
• CAS No.: 83051-84-7
• Molecular Formula: C₂₃H₃₁NO₉
• Molecular Weight: 465.5
• Mol file: 83051-84-7.mol

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

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

There total 6 articles about 7-O-acetyl-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: 86.0%

acetic acid (64-19-7,77671-22-8) + 6,7-(N-benzyloxycarbonyl)epimino-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose (76951-85-4,76951-91-2) → 7-O-acetyl-6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose (83051-84-7)

Guidance literature:

at 50 ℃; for 2h;

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) → 7-O-acetyl-6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose (83051-84-7)

Guidance literature:

Multi-step reaction with 4 steps

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

2: lithium aluminium hydride

3: benzyloxycarbonylating agent / H₂O; dioxane

With lithium aluminium tetrahydride; benzyloxycarbonylating 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) → 7-O-acetyl-6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose (83051-84-7)

Guidance literature:

Multi-step reaction with 2 steps

1: benzyloxycarbonylating agent / H₂O; dioxane

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

DOI:10.1246/cl.1980.1439

upstream raw materials:

acetic acid

6,7-(N-benzyloxycarbonyl)epimino-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose

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

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

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

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

6-N,7-O-carbonyl-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose