1,2:5,6-Di-O-isopropylidene-3-O-tosyl-α-D-gulofuranose

Base Information

• Chemical Name: 1,2:5,6-Di-O-isopropylidene-3-O-tosyl-α-D-gulofuranose
• CAS No.: 19131-06-7
• Molecular Formula: C₁₉H₂₆O₈S
• Molecular Weight: 414.477
• Mol file: 19131-06-7.mol

Synonyms:1,2:5,6-Di-O-isopropylidene-3-O-tosyl-α-D-gulofuranose;1,2:5,6-Bis-O-(1-Methylethylidene)-α-D-gulofuranose 4-Methylbenzenesulfonate

Chemical Property of 1,2:5,6-Di-O-isopropylidene-3-O-tosyl-α-D-gulofuranose

Chemical Property:

• PSA: 97.90000
• LogP: 3.17760
• Solubility.: Chloroform, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

1,2:5,6-Di-O-isopropylidene-3-O-tosyl-α-D-gulofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 1,2:5,6-Di-O-isopropylidene-3-O-tosyl-α-D-gulofuranose (cas# 19131-06-7) is a compound useful in organic synthesis.

Technology Process of 1,2:5,6-Di-O-isopropylidene-3-O-tosyl-α-D-gulofuranose

There total 13 articles about 1,2:5,6-Di-O-isopropylidene-3-O-tosyl-α-D-gulofuranose 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%

(3aR,5S,6S,6aR)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol (582-52-5,2595-05-3,10368-86-2,13100-30-6,14686-89-6,23262-79-5,26597-74-0,26623-15-4,38166-58-4,38166-60-8,79943-22-9,83730-28-3) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (3aS,5S,6R,6aS)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (3253-75-6,13964-21-1,19131-06-7,23344-48-1,26597-75-1,28140-21-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 25 ℃; for 24h; Yields of byproduct given;

DOI:10.1016/S0040-4039(01)80237-9

Reference yield: 95.0%

p-toluenesulfonyl chloride (98-59-9) + Diacetone D-glucose (2595-05-3) → 1,2,5,6-di-O-isopropylidene-3-O-(p-toluenesulfonyl)-α-D-allofuranose (3253-75-6,13964-21-1,19131-06-7,23344-48-1,26597-75-1,28140-21-8)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1016/S0040-4020(99)00575-X

Reference yield: 83.0%

1,2:5,6-Di-O-isopropyliden-3-O-(p-tolylsulfinyl)-α-D-allofuranose (79378-73-7) → 1,2,5,6-di-O-isopropylidene-3-O-(p-toluenesulfonyl)-α-D-allofuranose (3253-75-6,13964-21-1,19131-06-7,23344-48-1,26597-75-1,28140-21-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 1.5h;

upstream raw materials:

1,2 5,6-O-di(isopropylidene)-α-D-allofuranose

p-toluenesulfonyl chloride

1,2:5,6-Di-O-isopropyliden-3-O-(p-tolylsulfinyl)-α-D-allofuranose

(1,2:5,6)-di-O-isopropylidene-D-gulose

Downstream raw materials:

[(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester

[(3aR,5S,6S,6aR)-5-((R)-1-Hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester

[(3aR,5S,6S,6aR)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester

[(3aR,5S,6S,6aR)-5-((S)-1-Hydroxy-2-iodo-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester

Refernces

• 1、 Arat, Esra,Bulut, Adnan,Demirta?, ?brahim,I??lar, ?zer,Sahin Yaglioglu, Ayse,Türk, Mustafa. "Synthesis and biological evaluation of novel urea, thiourea and squaramide diastereomers possessing sugar backbone". . . Retrieved 2020/04/08.
• 2、 Theoneste, Muhizi,Stephane, Greller,Veronique, Coma. "Synthesis and antibacterial activity of aminodeoxyglucose derivatives against Listeria innocua and Salmonella typhimurium". experimental part. p. 8770 - 8775. Retrieved 2010/07/17.