1,6-anhydro-4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose

Base Information

• Chemical Name: 1,6-anhydro-4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose
• CAS No.: 657395-01-2
• Molecular Formula: C₅₁H₄₇N₃O₁₁
• Molecular Weight: 877.948
• Mol file: 657395-01-2.mol

Synonyms:1,6-anhydro-4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose

Chemical Property of 1,6-anhydro-4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-anhydro-4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose

There total 17 articles about 1,6-anhydro-4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose 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: 61.0%

1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside (334834-19-4) + Benzoic acid (2R,3S,4R,5R)-5-azido-4-benzyloxy-3-(naphthalen-2-ylmethoxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-ylmethyl ester (657395-19-2) → 1,6-anhydro-4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose (657395-01-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate;

DOI:10.1002/jccs.200400175

Reference yield:

3-O-benzyl-1,6-anhydro-β-L-idopyranose (42926-91-0) → 1,6-anhydro-4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose (657395-01-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / pyridine

2: 61 percent / TMSOTf

With pyridine; trimethylsilyl trifluoromethanesulfonate;

DOI:10.1002/jccs.200400175

Reference yield:

6-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-α-D-glucofuranose (134198-40-6) → 1,6-anhydro-4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose (657395-01-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: t-BuOK / 2-methyl-propan-2-ol

1.2: 52 percent / aq. H₂SO₄ / bis-(2-methoxy-ethyl) ether / 160 °C

2.1: 85 percent / pyridine

3.1: 61 percent / TMSOTf

With pyridine; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; In tert-butyl alcohol;

DOI:10.1002/jccs.200400175

upstream raw materials:

1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside

Benzoic acid (2R,3S,4R,5R)-5-azido-4-benzyloxy-3-(naphthalen-2-ylmethoxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-ylmethyl ester

6-hydroxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranoside

6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-xylo-hex-5-enofuranose

Downstream raw materials:

C₅₅H₅₁Cl₃N₄O₁₃

4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphth-ylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl trichloroacetimidate

4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl levulinate

C₇₄H₇₂N₆O₁₈