Methyl(methyl3-deoxy-D-arabino-hept-2-ulopyranosid)onate

Base Information

• Chemical Name: Methyl(methyl3-deoxy-D-arabino-hept-2-ulopyranosid)onate
• CAS No.: 2880-95-7
• Molecular Formula: C9H16 O7
• Molecular Weight: 236.222
• Mol file: 2880-95-7.mol

Synonyms:D-arabino-Heptulopyranosidonicacid, methyl 3-deoxy-, methyl ester (7CI,8CI)

Chemical Property of Methyl(methyl3-deoxy-D-arabino-hept-2-ulopyranosid)onate

Chemical Property:

• Boiling Point: 385.4±42.0 °C(Predicted)
• PKA: 13.08±0.70(Predicted)
• PSA: 105.45000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: -1.99490

Purity/Quality:

METHYL-(METHYL-3-DEOXY-D-ARABINO-HEPT-2-ULOPYRANOSID)ONATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl(methyl3-deoxy-D-arabino-hept-2-ulopyranosid)onate

There total 16 articles about Methyl(methyl3-deoxy-D-arabino-hept-2-ulopyranosid)onate 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: 94.0%

methyl 3-deoxy-4,5:6,7-di-O-isopropylidene-D-arabino-hept-2-ulosonate (91294-65-4) → methyl (methyl 3-deoxy-α-D-arabino-2-heptulopyranosid)onate (2880-95-7,85549-51-5)

Guidance literature:

With hydrogenchloride; In methanol; Heating;

DOI:10.1021/ja00285a022

Reference yield: 90.0%

(2R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (85464-51-3) → methyl (methyl 3-deoxy-α-D-arabino-2-heptulopyranosid)onate (2880-95-7,85549-51-5)

Guidance literature:

With sodium hydrogencarbonate; In methanol; for 1h; Ambient temperature;

DOI:10.1016/S0008-6215(96)00227-3

Reference yield: 88.0%

methanol (67-56-1) + (4R,5S,6R)-2,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-carboxylic acid methyl ester → methyl (methyl 3-deoxy-α-D-arabino-2-heptulopyranosid)onate (2880-95-7,85549-51-5) + methyl (methyl 3-deoxy-D-arabino-2-heptulofuranosid)onate

Guidance literature:

With Amberlite IR-120 (H⁺); for 18h; Yields of byproduct given; Heating;

upstream raw materials:

methanol

methyl 3-deoxy-4,5:6,7-di-O-isopropylidene-D-arabino-hept-2-ulosonate

(2R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-arabino-hept-2-ulopyranosid)onate

Downstream raw materials:

diphenyl 7-phosphate

(2R,3S,4R)-6,7-Bis-(phenyl-hydrazono)-heptane-1,2,3,4-tetraol

Methyl (methyl 4,5-di-O-acetyl-7-O-trityl-3-deoxy-D-arabino-heptulopyranosid)onate

methyl (methyl 5,7-O-benzylidene-3-deoxy-D-ribo-heptulopyranosid)onate

Refernces

• 1、 Mikshiev,Kornilov,Paidak,Zhdanov. "Synthesis of higher 3-deoxy-2-ketoaldonic acids by construction and deoximation of their hydroxyiminoesters". . p. 476 - 482. Retrieved 2007/10/03.
• 2、 Mlynarski, Jacek,Banaszek, Anna. "A novel chemical synthesis of a 3-deoxy-D-arabino-heptulosonic acid 7-phosphate (DAHP) derivative and its 2-deoxy analogue". . p. 69 - 75. Retrieved 2007/10/03.