2,6-anhydro-1,3,4-trideoxy-4-O-(phenylmethyl)-D-arabino-heptitol 6-methylbenzenesulfonate

Base Information

• Chemical Name: 2,6-anhydro-1,3,4-trideoxy-4-O-(phenylmethyl)-D-arabino-heptitol 6-methylbenzenesulfonate
• CAS No.: 544704-44-1
• Molecular Formula: C₂₁H₂₆O₅S
• Molecular Weight: 390.5
• Mol file: 544704-44-1.mol

Synonyms:2,6-anhydro-1,3,4-trideoxy-4-O-(phenylmethyl)-D-arabino-heptitol 6-methylbenzenesulfonate

Chemical Property of 2,6-anhydro-1,3,4-trideoxy-4-O-(phenylmethyl)-D-arabino-heptitol 6-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,6-anhydro-1,3,4-trideoxy-4-O-(phenylmethyl)-D-arabino-heptitol 6-methylbenzenesulfonate

There total 2 articles about 2,6-anhydro-1,3,4-trideoxy-4-O-(phenylmethyl)-D-arabino-heptitol 6-methylbenzenesulfonate 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:

p-toluenesulfonyl chloride (98-59-9) + 2,6-anhydro-1,3,4-trideoxy-4,6-O-(phenylmethylene)-D-arabino-heptitol (544704-40-7) → 2,6-anhydro-1,3,4-trideoxy-6-O-(phenylmethyl)-D-arabino-heptitol + 2,6-anhydro-1,3,4-trideoxy-4-O-(phenylmethyl)-D-arabino-heptitol 6-methylbenzenesulfonate (544704-44-1)

Guidance literature:

2,6-anhydro-1,3,4-trideoxy-4,6-O-(phenylmethylene)-D-arabino-heptitol; With diisobutylaluminium hydride; In toluene; at 20 ℃; for 24h;

p-toluenesulfonyl chloride; With dmap; triethylamine; In dichloromethane; for 40h; Heating;

DOI:10.1016/S0957-4166(03)00126-5

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 2,6-anhydro-1,3,4-trideoxy-4-O-(phenylmethyl)-D-arabino-heptitol 6-methylbenzenesulfonate (544704-44-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 94 percent / p-toluenesulfonic acid / acetonitrile / 4 h / 20 °C

2.1: diisobutylaluminum hydride / toluene / 24 h / 20 °C

2.2: 2.70 g / 4-(N,N-dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 40 h / Heating

With diisobutylaluminium hydride; toluene-4-sulfonic acid; In toluene; acetonitrile;

DOI:10.1016/S0957-4166(03)00126-5

Reference yield: 84.0%

sodium cyanide (143-33-9,25596-52-5) + 2,6-anhydro-1,3,4-trideoxy-4-O-(phenylmethyl)-D-arabino-heptitol 6-methylbenzenesulfonate (544704-44-1) → 6-methyl-3-(phenylmethoxy)-tetrahydro-2H-pyran-2-acetonitrile (544704-46-3)

Guidance literature:

With sodium iodide; In N,N-dimethyl-formamide; at 80 ℃; for 14h;

DOI:10.1016/S0957-4166(03)00126-5

upstream raw materials:

p-toluenesulfonyl chloride

2,6-anhydro-1,3,4-trideoxy-4,6-O-(phenylmethylene)-D-arabino-heptitol

benzaldehyde dimethyl acetal

Downstream raw materials:

6-methyl-3-(phenylmethoxy)-tetrahydro-2H-pyran-2-acetonitrile

1-[(2R,3S,6R)-tetrahydro-6-methyl-3-(phenylmethoxy)-2H-pyran-2-yl]-2-propanone

2-((3S,6R)-3-Benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethanol