O-<2-(benzenesulfonamido)-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl>-β-(1<*>4)-1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabinohex-1-enopyranose

Base Information

• Chemical Name: O-<2-(benzenesulfonamido)-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl>-β-(1<*>4)-1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabinohex-1-enopyranose
• CAS No.: 128358-52-1
• Molecular Formula: C₅₃H₅₁NO₁₂S
• Molecular Weight: 926.053
• Mol file: 128358-52-1.mol

Synonyms:O-<2-(benzenesulfonamido)-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl>-β-(1<*>4)-1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabinohex-1-enopyranose

Chemical Property of O-<2-(benzenesulfonamido)-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl>-β-(1<*>4)-1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabinohex-1-enopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-<2-(benzenesulfonamido)-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl>-β-(1<*>4)-1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabinohex-1-enopyranose

There total 2 articles about O-<2-(benzenesulfonamido)-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl>-β-(1<*>4)-1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabinohex-1-enopyranose 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:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → O-<2-(benzenesulfonamido)-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl>-β-(1<*>4)-1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabinohex-1-enopyranose (128358-52-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / iodonium di-sym-collidine perchlorate, 4-A molecular sieves / CH₂Cl₂ / 0 °C

2: 1.) lithium tetramethylpiperidine, 2.) silver trifluoromethanesulfonate / 1.) THF, -78 deg C, 10 min, 2.) from -78 deg C to RT

With iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; 2,2,6,6-tetramethylpiperidinyl-lithium; silver trifluoromethanesulfonate; In dichloromethane;

DOI:10.1021/ja00171a021

Reference yield:

1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol (58871-06-0) + N-(3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-mannopyranosyl)benzenesulfonamide (128358-45-2) → O-<2-(benzenesulfonamido)-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl>-β-(1<*>4)-1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabinohex-1-enopyranose (128358-52-1)

Guidance literature:

With 2,2,6,6-tetramethylpiperidinyl-lithium; silver trifluoromethanesulfonate; Yield given. Multistep reaction; 1.) THF, -78 deg C, 10 min, 2.) from -78 deg C to RT;

DOI:10.1021/ja00171a021

upstream raw materials:

1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol

N-(3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-mannopyranosyl)benzenesulfonamide

3,4,6-tri-O-benzyl-D-glucal