[[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]methyl] phosphono hydrogen phosphate

Base Information

• Chemical Name: [[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]methyl] phosphono hydrogen phosphate
• CAS No.: 30174-43-7
• Molecular Formula: C₁₅H₂₄N₂O₁₆P₂
• Molecular Weight: 550.307
• DSSTox Substance ID: DTXSID90952569
• Mol file: 30174-43-7.mol

Synonyms:URDP;uridine 5'-(beta-rhamnopyranosyl diphosphate)

Chemical Property of [[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]methyl] phosphono hydrogen phosphate

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 307.64000
• Density: 1.959g/cm³
• LogP: -3.96700
• XLogP3: -6.7
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 7
• Exact Mass: 550.06010668
• Heavy Atom Count: 35
• Complexity: 957

Purity/Quality:

99% ^*data from raw suppliers

UDP-a-L-rhamnose sodium salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)C(C2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)OP(=O)(O)OP(=O)(O)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H](C(O1)C([C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)OP(=O)(O)OP(=O)(O)O)O)O)O

Technology Process of [[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]methyl] phosphono hydrogen phosphate

There total 36 articles about [[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]methyl] phosphono hydrogen phosphate 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: 68.0%

D-Fucose (73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6) + uridine 5'-triphosphate trisodium salt (1476-50-2,14264-46-1,19817-92-6,36051-69-1,74674-72-9) → UDP-6-deoxy-Gal (16375-63-6,30174-43-7)

Guidance literature:

With pyrophosphatase, inorganic from yeast; UTP-glucose-1-phosphate galactokinase from Streptococcus pneumoniae TIGR₄; UTP-glucose-1-phosphate uridylyltransferase from Streptococcus pneumoniae TIGR₄; adenosine 5'-triphosphate sodium salt; magnesium chloride; In aq. buffer; at 42 ℃; for 24h; pH=8; Enzymatic reaction;

DOI:10.1016/j.carres.2013.03.005

Reference yield:

→ diphosphoric acid-1-β-L-rhamnopyranosyl ester-2-uridin-5'-yl ester (1955-26-6,30174-43-7)

Guidance literature:

mit Hilfe von Enzym-Praeparaten aus den Blaettern von Phaseolus aureus;

DOI:10.1016/0006-291X(62)90264-4

Reference yield:

D-Fucose (73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6) + UTP (63-39-8) → UDP-6-deoxy-Gal (16375-63-6,30174-43-7)

Guidance literature:

With pyrophosphatase; Streptococcus pneumoniae TIGR₄ galactokinase; Arabidopsis thaliana uridine-diphosphate-sugar pyrophosphorylase; ATP; magnesium chloride; In aq. buffer; at 42 ℃; for 1h; pH=8; Enzymatic reaction;

DOI:10.1016/j.bmcl.2013.04.090

upstream raw materials:

6-Desoxy-α-D-glucopyranosyl-phosphat

uridine

6-deoxy-D-glucose

methyl-alpha-D-glucopyranoside

Refernces

• 1、 Zou, Yang,Xue, Mengyang,Wang, Wenjun,Cai, Li,Chen, Leilei,Liu, Jun,Wang, Peng George,Shen, Jie,Chen, Min. "One-pot three-enzyme synthesis of UDP-Glc, UDP-Gal, and their derivatives". supporting information. p. 76 - 81. Retrieved 2013/06/27.
• 2、 Timmons, Shannon C.,Jakeman, David L.. "Stereoselective chemical synthesis of sugar nucleotides via direct displacement of acylated glycosyl bromides". . p. 1227 - 1230. Retrieved 2007/10/03.