3-O-benzyl-1,2-O-isopropylidene-(6S,7R)-diacetoxy-5,8-dideoxy-5,8-(N-benzylimino)-α-D-erythro-L-ido-octa-1,4-furanose

Base Information

• Chemical Name: 3-O-benzyl-1,2-O-isopropylidene-(6S,7R)-diacetoxy-5,8-dideoxy-5,8-(N-benzylimino)-α-D-erythro-L-ido-octa-1,4-furanose
• CAS No.: 909705-94-8
• Molecular Formula: C₂₉H₃₅NO₈
• Molecular Weight: 525.599
• Mol file: 909705-94-8.mol

Synonyms:3-O-benzyl-1,2-O-isopropylidene-(6S,7R)-diacetoxy-5,8-dideoxy-5,8-(N-benzylimino)-α-D-erythro-L-ido-octa-1,4-furanose

Chemical Property of 3-O-benzyl-1,2-O-isopropylidene-(6S,7R)-diacetoxy-5,8-dideoxy-5,8-(N-benzylimino)-α-D-erythro-L-ido-octa-1,4-furanose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-1,2-O-isopropylidene-(6S,7R)-diacetoxy-5,8-dideoxy-5,8-(N-benzylimino)-α-D-erythro-L-ido-octa-1,4-furanose

There total 1 articles about 3-O-benzyl-1,2-O-isopropylidene-(6S,7R)-diacetoxy-5,8-dideoxy-5,8-(N-benzylimino)-α-D-erythro-L-ido-octa-1,4-furanose 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: 73.0%

3-O-benzyl-1,2-O-isopropylidene-5,8-dideoxy-5,8-(N-benzylamino)-di-hydroxy-α-L-erythro-L-ido-octa-1,4-furanose + acetic anhydride (108-24-7) → 3-O-benzyl-1,2-O-isopropylidene-(6S,7R)-diacetoxy-5,8-dideoxy-5,8-(N-benzylimino)-α-D-erythro-L-ido-octa-1,4-furanose (909705-94-8) + 3-O-benzyl-1,2-O-isopropylidene-(6R,7S)-diacetoxy-5,8-dideoxy-5,8-(N-benzylimino)-α-L-erythro-L-ido-octa-1,4-furanose (909705-93-7)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 6h;

DOI:10.1021/jo060823s

Reference yield: 90.0%

3-O-benzyl-1,2-O-isopropylidene-(6S,7R)-diacetoxy-5,8-dideoxy-5,8-(N-benzylimino)-α-D-erythro-L-ido-octa-1,4-furanose (909705-94-8) → 3-O-benzyl-1,2-O-isopropylidene-5,8-dideoxy-5,8-(N-benzylamino)-6(S),7(R)-di-hydroxy-α-D-erythro-L-ido-octa-1,4-furanose (909705-96-0)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 2h;

DOI:10.1021/jo060823s

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-(6S,7R)-diacetoxy-5,8-dideoxy-5,8-(N-benzylimino)-α-D-erythro-L-ido-octa-1,4-furanose (909705-94-8) → 5,8-dideoxy-5,8-(N-benzoxycarbonylimino)-1,2-O-isopropylidene-(6S,7R)-dihydroxy-α-D-erythro-L-ido-octa-1,4-furanose (909705-98-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / sodium methoxide / methanol / 2 h / 0 °C

2: ammonium formate / palladium on carbon / methanol / 1 h / 80 °C

3: 0.20 g / sodium hydrogen carbonate / methanol; H₂O / 2 h / 20 °C

With sodium methylate; ammonium formate; sodium hydrogencarbonate; palladium on activated charcoal; In methanol; water;

DOI:10.1021/jo060823s

upstream raw materials:

acetic anhydride

Downstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-5,8-dideoxy-5,8-(N-benzylamino)-6(S),7(R)-di-hydroxy-α-D-erythro-L-ido-octa-1,4-furanose

5,8-dideoxy-5,8-(N-benzoxycarbonylimino)-1,2-O-isopropylidene-(6S,7R)-dihydroxy-α-D-erythro-L-ido-octa-1,4-furanose