[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl (2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name)

Base Information

• Chemical Name: [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl (2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name)
• CAS No.: 62012-79-7
• Molecular Formula: C16H26N2O15P2
• Molecular Weight: 548.3296
• Mol file: 62012-79-7.mol

Synonyms:

Chemical Property of [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl (2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name)

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.78g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl (2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name)

There total 35 articles about [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl (2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name) 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: 90.0%

thymidine 5'-(α-D-glucopyranosyl diphosphate) (2196-62-5) → TDP-6-deoxy-D-gulose (62012-79-7)

Guidance literature:

With Salmonella enterica RfbB enzyme; Salmonella enterica RfbC enzyme; Salmonella enterica RfbD enzyme; alcohol dehydrogenase; In isopropyl alcohol; at 37 ℃; for 2.5h; pH=7.5;

DOI:10.1002/anie.200503195

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

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