methyl D-glucopyranuronate

Base Information

• Chemical Name: methyl D-glucopyranuronate
• CAS No.: 82228-14-6
• Molecular Formula: C₇H₁₂O₇
• Molecular Weight: 208.168
• Mol file: 82228-14-6.mol

Synonyms:methyl D-glucopyranuronate

Chemical Property of methyl D-glucopyranuronate

Chemical Property:

• Boiling Point: 372.0±42.0 °C(Predicted)
• Density: 1.691±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

Methyl Raloxifene-d4 4’- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: D-Glucuronide Methyl Ester is an intermediate used in the synthesis of 2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester Trichloroacetimidate (T765200), which is an intermediate for the synthesis of various glucuronide derivatives

Technology Process of methyl D-glucopyranuronate

There total 24 articles about methyl D-glucopyranuronate 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: 56.0%

methanol (67-56-1) + 2,3,4-tri-O-acetyl-β-D-glucopyranurono-6,1-lactone (82970-25-0) → methyl D-glucopyranuronate (82228-14-6)

Guidance literature:

With toluene-4-sulfonic acid; at 65 ℃; for 0.0333333h; microwave irradiation;

DOI:10.1016/j.tet.2007.09.043

Reference yield:

3-O-[α-L-rhamnopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→3)-β-D-glucopyranosyl-(1→2)-β-D-(6′-O-methyl)glucuronopyranosyl]-13β,28-epoxy-3β,16α-dihydroxy-olean → D-Glucose (2280-44-6) + D-Galactose (10257-28-0) + L-rhamnose (73-34-7) + methyl D-glucopyranuronate (82228-14-6)

Guidance literature:

3-O-[α-L-rhamnopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→3)-β-D-glucopyranosyl-(1→2)-β-D-(6′-O-methyl)glucuronopyranosyl]-13β,28-epoxy-3β,16α-dihydroxy-olean; With hydrogenchloride; In 1,4-dioxane; at 60 ℃; for 2h;

With pyridine; perdeuteriopyridine; L-cysteine methyl ester hydrochloride; at 60 ℃; for 2h;

With 1-(Trimethylsilyl)imidazole; at 60 ℃; for 1.5h;

DOI:10.1007/s00044-020-02613-5

Reference yield:

methanol (67-56-1) + prosapogenin methyl ester → methyl D-galactopyranoside (97-30-3,617-04-9,709-50-2,1824-94-8,2152-78-5,3149-68-6,3396-99-4,6819-48-3,18469-06-2,20550-04-3,22277-65-2,29411-57-2,35437-40-2,35437-43-5,36191-11-4,36191-12-5,39598-79-3,39598-80-6,39598-89-5,51023-63-3,51223-62-2,51224-38-5,51224-39-6,51224-40-9,51224-41-0,51819-81-9,51819-82-0,51819-83-1,56688-81-4,62279-53-2,64281-79-4,64281-80-7,64912-19-2,66101-73-3,78184-90-4,84368-39-8,84368-40-1,84368-41-2,92142-37-5,93302-26-2,103421-28-9,115794-08-6) + methyl D-glucopyranuronate (82228-14-6) + quillaic acid methyl ester (6151-28-6,42483-23-8) + C38H58O11

Guidance literature:

With hydrogenchloride; for 7h; Ambient temperature;

upstream raw materials:

methanol

D-galacturonic acid

(3aR,5S,5aR,8aS,8bR)-methyl-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-carboxylate

D-galacturonic acid

Downstream raw materials:

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl 1,2,3,4-tetra-O-isobutyryl-β-D-glucopyranuronate

(2S,3S,4S,5R)-3,4,5,6-Tetrakis-benzoyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Refernces

• 1、 Vinh, Le Ba,Phong, Nguyen Viet,Ali, Irshad,Dan, Gao,Koh, Young Sang,Anh, Hoang Le Tuan,Van Anh, Do Thi,Yang, Seo Young,Kim, Young Ho. "Identification of potential anti-inflammatory and melanoma cytotoxic compounds from Aegiceras corniculatum". . p. 2020 - 2027. Retrieved 2020/09/01.
• 2、 Hou, Zhuang,Liu, Yang,Zhang, Xin-xin,Chang, Xiao-wei,Cheng, Mao-sheng,Guo, Chun. "Synthesis of glucuronic acid derivatives via the efficient and selective removal of a C6 methyl group". supporting information. p. 423 - 426. Retrieved 2017/01/10.