5-(p-Toluenesulfonate)-2,3-O-isopropylidene-2-C-methyl-D-ribonic-gamma-lactone

Base Information

• Chemical Name: 5-(p-Toluenesulfonate)-2,3-O-isopropylidene-2-C-methyl-D-ribonic-gamma-lactone
• CAS No.: 109715-12-0
• Molecular Formula: C16H20 O7 S
• Molecular Weight: 342.366
• Mol file: 109715-12-0.mol

Synonyms:5-(p-Toluenesulfonate)-2,3-O-isopropylidene-2-C-methyl-D-ribonic-gamma-lactone;5-(p-Toluenesulfonate)-2,3-O-isopropylidene-2-C-methyl-D-ribonic-γ-lactone

Chemical Property of 5-(p-Toluenesulfonate)-2,3-O-isopropylidene-2-C-methyl-D-ribonic-gamma-lactone

Chemical Property:

• PSA: 96.51000
• Density: 1.293
• LogP: 2.22660

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-(p-Toluenesulfonate)-2,3-O-isopropylidene-2-C-methyl-D-ribonic-gamma-lactone

There total 2 articles about 5-(p-Toluenesulfonate)-2,3-O-isopropylidene-2-C-methyl-D-ribonic-gamma-lactone 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:

2-methyl-2,3-O-(1-methylethylidene)-D-ribonic acid γ-lactone (23709-41-3) + p-toluenesulfonyl chloride (98-59-9) → 2,3-O-Isopropyliden-2-C-methyl-5-O-p-toluolsulfonyl-D-ribo-pentonsaeure-γ-lacton (109715-12-0)

Guidance literature:

With pyridine;

Reference yield:

→ 2,3-O-Isopropyliden-2-C-methyl-5-O-p-toluolsulfonyl-D-ribo-pentonsaeure-γ-lacton (109715-12-0)

Guidance literature:

2,3-O-Isopropyliden-α-D-glucosaccharin, p-Toluolsulfonylchlorid in Py.;

DOI:10.1021/ja01499a059

Reference yield: 94.0%

2,3-O-Isopropyliden-2-C-methyl-5-O-p-toluolsulfonyl-D-ribo-pentonsaeure-γ-lacton (109715-12-0) → 2,3-O-isopropylidene-2-C-methyl-5-O-p-tolylsulfonyl-D-ribofuranose

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 1h; Optical yield = 33.333 %de; Inert atmosphere;

DOI:10.1002/ejoc.201301705

upstream raw materials:

2-methyl-2,3-O-(1-methylethylidene)-D-ribonic acid γ-lactone

p-toluenesulfonyl chloride

Downstream raw materials:

(-)-(2S,3R)-1-O-benzoyl-2,3-dihydroxy-2,3-O-isopropylidene-2-methylpent-4-ene

(-)-(2S,3S)-4-O-benzoyl-2,3-dihydroxy-2,3-O-isopropylidene-2-methylbutanal

(-)-(2S,3R)-5-(2,5-dimethoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidene-4-methylpentene

(-)-(2S,3S)-4-(2,5-dimethoxyphenyl)-2,3-dihydroxy-2,3-O-isopropylidene-3-methylbutanal

Refernces

• 1、 Lopez-Herrera, F. J.,Sarabia-Garcia, F.,Pino-Gonzalez, M. S.,Garcia-Aranda, J. F.. "A NEW SYMTHESIS OF 2-C-METHYL-D-RIBONO-1,4-LACTONE AND THE C-9/C-13 FRAGMENT OF METHYNOLIDE". . p. 767 - 776. Retrieved 2007/10/02.