3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-imino-1-O-(p-toluenesulfonyl)-D-glycero-D-gulo-heptitol

Base Information

• Chemical Name: 3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-imino-1-O-(p-toluenesulfonyl)-D-glycero-D-gulo-heptitol
• CAS No.: 162333-07-5
• Molecular Formula: C₄₂H₄₅NO₇S
• Molecular Weight: 707.888
• Mol file: 162333-07-5.mol

Synonyms:3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-imino-1-O-(p-toluenesulfonyl)-D-glycero-D-gulo-heptitol

Chemical Property of 3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-imino-1-O-(p-toluenesulfonyl)-D-glycero-D-gulo-heptitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-imino-1-O-(p-toluenesulfonyl)-D-glycero-D-gulo-heptitol

There total 9 articles about 3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-imino-1-O-(p-toluenesulfonyl)-D-glycero-D-gulo-heptitol 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: 93.0%

p-toluenesulfonyl chloride (98-59-9) + 3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-imino-D-glycero-D-gulo-heptitol (162428-42-4) → 3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-imino-1-O-(p-toluenesulfonyl)-D-glycero-D-gulo-heptitol (162333-07-5)

Guidance literature:

With n-butyllithium;

DOI:10.1016/0040-4039(94)02389-S

Reference yield:

3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-imino-1-O-(methoxymethyl)-D-glycero-D-gulo-heptitol (162333-05-3) → 3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-imino-1-O-(p-toluenesulfonyl)-D-glycero-D-gulo-heptitol (162333-07-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / aq. HCl / tetrahydrofuran; H₂O / 50 °C

2: 73 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

With hydrogenchloride; dmap; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo960362i

Reference yield:

(2R,3R,4S,5S)-1,3,4,5-Tetrakis-benzyloxy-7-methoxymethoxy-heptane-2,6-diol → 3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-imino-1-O-(p-toluenesulfonyl)-D-glycero-D-gulo-heptitol (162333-07-5)

Guidance literature:

Multi-step reaction with 4 steps

1: (CF₃CO)2O, DMSO / CH₂Cl₂ / 1.5 h / -78 °C

2: ammonium formate, NaBH₃CN / methanol / 0.5 h / Ambient temperature

3: 93 percent / aq. HCl / tetrahydrofuran; H₂O / 50 °C

4: 73 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

With hydrogenchloride; dmap; ammonium formate; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jo960362i

upstream raw materials:

p-toluenesulfonyl chloride

3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-imino-D-glycero-D-gulo-heptitol

3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-imino-1-O-(methoxymethyl)-D-glycero-D-gulo-heptitol

3,4,5,7-tetra-O-benzyl-1-O-(methoxymethyl)-D-xylo-2,6-heptodiulose

Downstream raw materials:

(2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxymethyl)-piperidine