2'-Deoxy-thymidine-beta-L-rhamnose

Base Information

• Chemical Name: 2'-Deoxy-thymidine-beta-L-rhamnose
• CAS No.: 2147-59-3
• Molecular Formula: C16H26N2O15P2
• Molecular Weight: 548.334
• DSSTox Substance ID: DTXSID50175752
• Nikkaji Number: J818.234E
• Wikidata: Q27098225
• Metabolomics Workbench ID: 50254
• Mol file: 2147-59-3.mol

Synonyms:dTDP-L-rhamnose;thymidine diphosphate rhamnose;thymidine diphosphate-L-rhamnose

Chemical Property of 2'-Deoxy-thymidine-beta-L-rhamnose

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 1.10±0.50(Predicted)
• Flash Point: °C
• PSA: 276.15000
• Density: 1.78g/cm³
• LogP: -2.42850
• XLogP3: -4.8
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 8
• Exact Mass: 548.08084212
• Heavy Atom Count: 35
• Complexity: 961

Purity/Quality:

99%, ^*data from raw suppliers

Thymidine-5?-diphosphate-L-rhamnosedisodiumsalt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OP(=O)(O)OP(=O)(O)OCC2C(CC(O2)N3C=C(C(=O)NC3=O)C)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H](C[C@@H](O2)N3C=C(C(=O)NC3=O)C)O)O)O)O

Technology Process of 2'-Deoxy-thymidine-beta-L-rhamnose

There total 9 articles about 2'-Deoxy-thymidine-beta-L-rhamnose 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: 63.0%

dTTP (365-08-2,92627-33-3,106119-81-7) + α-D-glucopyranosyl-1-phosphate (59-56-3,27251-84-9,63779-58-8,262856-84-8) → thymidine 5'-diphospho-β-L-rhamnose (2147-59-3,62012-79-7)

Guidance literature:

dTTP; α-D-glucopyranosyl-1-phosphate; With Streptococcus pneumonia serotype 23F Glc-1-P thymidylyltransferase Cps₂₃FL; nicotinamide adenine dinucleotide; β-nicotinamide adenine dinucleotide, disodium salt, reduced form; magnesium chloride; In aq. buffer; at 37 ℃; for 0.25h; pH=7.5; Enzymatic reaction;

With Streptococcus pneumonia serotype 23F dTDP-4-keto-6-deoxy-Glc-3,5-epimerase Cps₂₃FM; Streptococcus pneumonia serotype 23F dTDP-4-keto-Rham reductase Cps₂₃FO; Streptococcus pneumonia serotype 23F dTDP-Glc-4,6-dehydratase Cps₂₃FN; In aq. buffer; for 1h; pH=7.5; Enzymatic reaction;

DOI:10.1039/c6cc08366h

Reference yield:

O5'-(hydroxy-imidazol-1-yl-phosphinoyl)-thymidine (59373-11-4) + β-L-rhamnose 1-phosphate bis(triethylammonium) salt → thymidine 5'-phosphate (365-07-1,15108-71-1,60363-32-8,96744-88-6,132696-16-3,143838-77-1) + 2-deoxythymidine diphosphate (491-97-4) + thymidine 5'-diphospho-β-L-rhamnose (2147-59-3,62012-79-7)

Guidance literature:

In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1021/jo981265n

Reference yield:

(4-Chloro-butyl)-methyl-phosphoramidic acid mono-[(3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester + β-L-rhamnose 1-phosphate bis(triethylammonium) salt → thymidine 5'-diphospho-β-L-rhamnose (2147-59-3,62012-79-7)

Guidance literature:

With tetrabutyl-ammonium chloride; In pyridine; at 20 ℃;

DOI:10.1021/ol0167309

upstream raw materials:

O^5'-(hydroxy-imidazol-1-yl-phosphinoyl)-thymidine

thymidine diphosphate 4-keto-6-deoxy-α-D-glucose

dTTP

α-D-glucopyranosyl-1-phosphate

Downstream raw materials:

C₃₀H₄₄O₉

phosphoramidon

2-deoxythymidine diphosphate

Refernces

• 1、 Chiu, Hsien-Tai,Weng, Chien-Pao,Lin, Yu-Chin,Chen, Kuan-Hung. "Target-specific identification and characterization of the putative gene cluster for brasilinolide biosynthesis revealing the mechanistic insights and combinatorial synthetic utility of 2-deoxy-l-fucose biosynthetic enzymes". supporting information. p. 1988 - 2006. Retrieved 2016/02/18.
• 2、 Zhao, Yongxin,Thorson, Jon S.. "A methodological comparison: The advantage of phosphorimidates in expanding the sugar nucleotide repertoire". . p. 7568 - 7572. Retrieved 2007/10/03.