3,6-anhydro-2-deoxy-4,5-O-isopropylidene-1-O-(methylsulfonyl)-7-O-trityl-D-allo-heptitol

Base Information

• Chemical Name: 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-1-O-(methylsulfonyl)-7-O-trityl-D-allo-heptitol
• CAS No.: 937251-02-0
• Molecular Formula: C₃₀H₃₄O₇S
• Molecular Weight: 538.662
• Mol file: 937251-02-0.mol

Synonyms:3,6-anhydro-2-deoxy-4,5-O-isopropylidene-1-O-(methylsulfonyl)-7-O-trityl-D-allo-heptitol

Chemical Property of 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-1-O-(methylsulfonyl)-7-O-trityl-D-allo-heptitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-1-O-(methylsulfonyl)-7-O-trityl-D-allo-heptitol

There total 2 articles about 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-1-O-(methylsulfonyl)-7-O-trityl-D-allo-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: 74.0%

2-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)ethanol (73485-68-4) + methanesulfonyl chloride (124-63-0) → 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-1-O-(methylsulfonyl)-7-O-trityl-D-allo-heptitol (937251-02-0)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2007.02.017

Reference yield:

methyl 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-7-O-trityl-D-allo-heptanoate (56752-57-9) → 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-1-O-(methylsulfonyl)-7-O-trityl-D-allo-heptitol (937251-02-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / LiAlH₄ / diethyl ether / 18 h / 20 °C

2: 74 percent / DMAP; pyridine / 2 h / 20 °C

With pyridine; dmap; lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1016/j.bmcl.2007.02.017

Reference yield: 83.0%

3,6-anhydro-2-deoxy-4,5-O-isopropylidene-1-O-(methylsulfonyl)-7-O-trityl-D-allo-heptitol (937251-02-0) → 3,6-anhydro-1-azido-1,2-dideoxy-4,5-O-isopropylidene-7-O-trityl-D-allo-heptitol (937251-03-1)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 100 ℃; for 7h;

DOI:10.1016/j.bmcl.2007.02.017

upstream raw materials:

2-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)ethanol

methanesulfonyl chloride

methyl 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-7-O-trityl-D-allo-heptanoate

Downstream raw materials:

3,6-anhydro-1-azido-1,2-dideoxy-4,5-O-isopropylidene-7-O-trityl-D-allo-heptitol

3,6-anhydro-1,2-dideoxy-1-(4,5-diethyl-1H-1,2,3-triazol-1-yl)-4,5-O-isopropylidene-7-O-trityl-D-allo-heptitol

3,6-anhydro-1,2-dideoxy-4,5-O-isopropylidene-1-(5-methyl-4-phenyl-1H-1,2,3-triazol-1-yl)-7-O-trityl-D-allo-heptitol

3,6-anhydro-1,2-dideoxy-4,5-O-isopropylidene-1-(4-methyl-5-phenyl-1H-1,2,3-triazol-1-yl)-7-O-trityl-D-allo-heptitol