2,6-anhydro-1-azido-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-guloheptitol

Base Information

• Chemical Name: 2,6-anhydro-1-azido-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-guloheptitol
• CAS No.: 204068-81-5
• Molecular Formula: C₃₅H₃₇N₃O₅
• Molecular Weight: 579.696
• Mol file: 204068-81-5.mol

Synonyms:2,6-anhydro-1-azido-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-guloheptitol

Chemical Property of 2,6-anhydro-1-azido-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-guloheptitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,6-anhydro-1-azido-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-guloheptitol

There total 3 articles about 2,6-anhydro-1-azido-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-guloheptitol 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: 76.0%

β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (89064-71-1) → 2,6-anhydro-1-azido-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-guloheptitol (204068-81-5)

Guidance literature:

β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside; With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 100 ℃; for 2h;

With sodium azide; In N,N-dimethyl-formamide; at 100 ℃; for 14h;

DOI:10.1021/jo0607156

Reference yield:

1-(O-p-toluenesulfonyl)-3,4,5,7-tetra-O-benzyl-2,6-anhydroglucoheptitol (204068-78-0) → 2,6-anhydro-1-azido-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-guloheptitol (204068-81-5)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1521-3773(19981231)37:24<3436::AID-ANIE3436>3.0.CO;2-Z

Reference yield:

2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose (113019-43-5,140397-45-1,140397-46-2,140397-47-3,140397-49-5,91738-17-9) → 2,6-anhydro-1-azido-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-guloheptitol (204068-81-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / LiBH₄ / tetrahydrofuran

2: pyridine

3: NaN₃ / dimethylformamide

With pyridine; lithium borohydride; sodium azide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1521-3773(19981231)37:24<3436::AID-ANIE3436>3.0.CO;2-Z

upstream raw materials:

1-(O-p-toluenesulfonyl)-3,4,5,7-tetra-O-benzyl-2,6-anhydroglucoheptitol

β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose

Downstream raw materials:

N-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-formamide

(2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-isocyanomethyl-tetrahydro-pyran