2,3-O-Isopropylidene-1,6-di-O-p-toluenesulfonyl-a-L-sorbofuranose

Base Information

• Chemical Name: 2,3-O-Isopropylidene-1,6-di-O-p-toluenesulfonyl-a-L-sorbofuranose
• CAS No.: 2484-55-1
• Molecular Formula: C23H28 O10 S2
• Molecular Weight: 528.601
• Mol file: 2484-55-1.mol

Synonyms:Sorbofuranose,2,3-O-isopropylidene-, 1,6-di-p-toluenesulfonate, a-L- (7CI,8CI); Furo[2,3-d]-1,3-dioxole, a-L-sorbofuranose deriv.

Chemical Property of 2,3-O-Isopropylidene-1,6-di-O-p-toluenesulfonyl-a-L-sorbofuranose

Chemical Property:

• Melting Point: 118-120°C
• Boiling Point: 690.1±50.0 °C(Predicted)
• PKA: 12.68±0.70(Predicted)
• PSA: 151.42000
• Density: 1.369±0.06 g/cm3(Predicted)
• LogP: 4.18330
• Solubility.: Chloroform, Methanol

Purity/Quality:

98%Min ^*data from raw suppliers

2,3-O-Isopropylidene-1,6-di-O-p-toluenesulfonyl-a-L-sorbofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Byproduct obtained during the production of Deoxynojirimycin 2,3-O-Isopropylidene-1,6-ditosyl-L-sorbose is used in the synthesis of oxy-bridged bicyclic aza-sugar and thio-sugar as potential glycosidase inhibitors.

Technology Process of 2,3-O-Isopropylidene-1,6-di-O-p-toluenesulfonyl-a-L-sorbofuranose

There total 1 articles about 2,3-O-Isopropylidene-1,6-di-O-p-toluenesulfonyl-a-L-sorbofuranose 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: 98.0%

p-toluenesulfonyl chloride (98-59-9) + 2,3-O-isopropylidene-α-L-sorbofuranose (17682-71-2) → 2,3-O-isopropylidene-1,6-bis-O-(p-toluenesulfonyl)-α-L-sorbofuranose (2484-55-1)

Guidance literature:

With pyridine; at 20 ℃; for 5h;

DOI:10.1016/j.carres.2006.06.002

Reference yield: 89.0%

2,3-O-isopropylidene-1,6-bis-O-(p-toluenesulfonyl)-α-L-sorbofuranose (2484-55-1) → 6-azido-6-deoxy-2,3-O-isopropylidene-1-O-(p-toluenesulfonyl)-α-L-sorbofuranose (910222-11-6)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 75 ℃; for 30h;

DOI:10.1016/j.carres.2006.06.002

Reference yield:

2,3-O-isopropylidene-1,6-bis-O-(p-toluenesulfonyl)-α-L-sorbofuranose (2484-55-1) → 2-methyl-3-pyridinol (1121-25-1,55780-69-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / NaN₃ / dimethylformamide / 30 h / 75 °C

2: 40.3 percent / LiAlH₄ / tetrahydrofuran / 30 h / Heating

3: Dowex 50(H+); H₂ / Pd(OH)2/C / H₂O / 30 h / 3102.89 Torr / pH 3 - 4

With lithium aluminium tetrahydride; sodium azide; Dowex 50(H+); hydrogen; palladium dihydroxide; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2006.06.002

upstream raw materials:

p-toluenesulfonyl chloride

2,3-O-isopropylidene-α-L-sorbofuranose

Downstream raw materials:

O²,O³-isopropylidene-6-iodo-O¹-(toluene-4-sulfonyl)-6-deoxy-α-L-sorbofuranose

6-azido-6-deoxy-2,3-O-isopropylidene-1-O-(p-toluenesulfonyl)-α-L-sorbofuranose

N-benzyloxycarbonyl-1,5,6-trideoxy-1,5-imino-D-glucitol

1,5,6-trideoxy-1,5-imino-D-glucitol hydrochloride

Refernces

• 1、 Lee, Cheang-Kuan. "2-Hexuloses: selective sulphonylation of O-isopropylidene derivatives of D-fructopyranose and L-sorbofuranose". . p. 255 - 262. Retrieved 2007/10/02.