4-O-acetyl-1,6-anhydro-3-{(1R)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptitol-1-C-yl}-2-[(N-benzyl-N-methoxy)amino]-2,3-dideoxy-β-D-galacto-hexopyranose

Base Information

• Chemical Name: 4-O-acetyl-1,6-anhydro-3-{(1R)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptitol-1-C-yl}-2-[(N-benzyl-N-methoxy)amino]-2,3-dideoxy-β-D-galacto-hexopyranose
• CAS No.: 860634-51-1
• Molecular Formula: C₃₃H₄₃NO₁₆
• Molecular Weight: 709.702
• Mol file: 860634-51-1.mol

Synonyms:4-O-acetyl-1,6-anhydro-3-{(1R)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptitol-1-C-yl}-2-[(N-benzyl-N-methoxy)amino]-2,3-dideoxy-β-D-galacto-hexopyranose

Chemical Property of 4-O-acetyl-1,6-anhydro-3-{(1R)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptitol-1-C-yl}-2-[(N-benzyl-N-methoxy)amino]-2,3-dideoxy-β-D-galacto-hexopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-acetyl-1,6-anhydro-3-{(1R)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptitol-1-C-yl}-2-[(N-benzyl-N-methoxy)amino]-2,3-dideoxy-β-D-galacto-hexopyranose

There total 1 articles about 4-O-acetyl-1,6-anhydro-3-{(1R)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptitol-1-C-yl}-2-[(N-benzyl-N-methoxy)amino]-2,3-dideoxy-β-D-galacto-hexopyranose 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: 100.0%

(2S,3R,4S,5R,6R)-2-{(R)-[(1R,2R,3R,4R,5R)-4-(Benzyl-methoxy-amino)-2-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl]-hydroxy-methyl}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol + acetic anhydride (108-24-7) → 4-O-acetyl-1,6-anhydro-3-{(1R)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptitol-1-C-yl}-2-[(N-benzyl-N-methoxy)amino]-2,3-dideoxy-β-D-galacto-hexopyranose (860634-51-1)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 48h;

DOI:10.1002/chem.200401301

Reference yield:

4-O-acetyl-1,6-anhydro-3-{(1R)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptitol-1-C-yl}-2-[(N-benzyl-N-methoxy)amino]-2,3-dideoxy-β-D-galacto-hexopyranose (860634-51-1) + phenylthiotrimethylsilane (4551-15-9) → Acetic acid (R)-[(2R,3R,4R,5R,6S)-3-acetoxy-5-(benzyl-methoxy-amino)-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-((2S,3S,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-methyl ester

Guidance literature:

4-O-acetyl-1,6-anhydro-3-{(1R)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptitol-1-C-yl}-2-[(N-benzyl-N-methoxy)amino]-2,3-dideoxy-β-D-galacto-hexopyranose; phenylthiotrimethylsilane; With zinc(II) iodide; In dichloromethane; at 20 ℃; for 2h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1002/chem.200401301

Reference yield:

4-O-acetyl-1,6-anhydro-3-{(1R)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptitol-1-C-yl}-2-[(N-benzyl-N-methoxy)amino]-2,3-dideoxy-β-D-galacto-hexopyranose (860634-51-1) → 4,6-di-O-acetyl-3-C-[(1R)-2,6-anhydro-1,3,4,5,7-penta-O-acetyl-D-glycero-L-manno-heptitol-1-C-yl]-2-[(N-benzyl-N-methoxy)amino]-2,3-dideoxy-β-D-galacto-hexopyranosyl phenylsulfide (860634-53-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ZnI₂ / CH₂Cl₂ / 2 h / 20 °C

1.2: TBAF / tetrahydrofuran / 1 h / 20 °C

2.1: 370 mg / pyridine; DMAP / 18 h / 20 °C

With pyridine; dmap; zinc(II) iodide; In dichloromethane;

DOI:10.1002/chem.200401301

upstream raw materials:

acetic anhydride

Downstream raw materials:

4,6-di-O-acetyl-3-C-[(1R)-2,6-anhydro-1,3,4,5,7-penta-O-acetyl-D-glycero-L-manno-heptitol-1-C-yl]-2-[(N-benzyl-N-methoxy)amino]-2,3-dideoxy-β-D-galacto-hexopyranosyl phenylsulfide