Thymidine, 5,6-dihydro-5,6-dihydroxy-, (5S,6R)-

Base Information

• Chemical Name: Thymidine, 5,6-dihydro-5,6-dihydroxy-, (5S,6R)-
• CAS No.: 38709-52-3
• Molecular Formula: C10H16N2O7
• Molecular Weight: 276.246
• DSSTox Substance ID: DTXSID30423788
• Nikkaji Number: J554.791A
• Wikidata: Q82236079
• Mol file: 38709-52-3.mol

Synonyms:Thymidine, 5,6-dihydro-5,6-dihydroxy-, (5S,6R)-;38709-52-3;(5S,6R)-Thymidine glycol;DTXSID30423788;RKEITGVZZHXKON-ZTOQJESFSA-N;(5S,6R)-5,6-Dihydroxy-5,6-dihydrothymidine

Chemical Property of Thymidine, 5,6-dihydro-5,6-dihydroxy-, (5S,6R)-

Chemical Property:

• XLogP3: -2.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 276.09575085
• Heavy Atom Count: 19
• Complexity: 403

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N(C(=O)NC1=O)C2CC(C(O2)CO)O)O)O
• Isomeric SMILES: C[C@@]1([C@H](N(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)O)O)O

Technology Process of Thymidine, 5,6-dihydro-5,6-dihydroxy-, (5S,6R)-

There total 8 articles about Thymidine, 5,6-dihydro-5,6-dihydroxy-, (5S,6R)- 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: 19.0%

trans-(5S,6S)-6-hydroxy-5-(2,2,6,6-tetramethyl-4-oxo-1-piperidinyl-N-oxide)-5,6-dihydrothymidine (96221-62-4,96290-63-0) → N1-(2-deoxy-β-D-erythro-pentofuranosyl)formamide (57609-73-1) + 1-(2-deoxy-β-D-erythro-pentafuranosyl)-5-hydroxy-5-methyl-hydantoin (127707-34-0,38716-09-5) + (+)-cis-(5S,6R)-5,6-dihydroxy-5,6-dihydrothymidine (38709-52-3) + (-)-cis-(5R,6S)-6-hydroxy-5,6-dihydrothymidine (32926-52-6,68509-78-4)

Guidance literature:

In pyridine; water; at 60 ℃; for 3h;

DOI:10.1139/v85-002

Reference yield: 19.0%

trans-(5R,6R)-6-hydroxy-5-(2,2,6,6-tetramethyl-4-oxo-1-piperidinyl-N-oxide)-5,6-dihydrothymidine (96221-62-4,96290-63-0) → N1-(2-deoxy-β-D-erythro-pentofuranosyl)formamide (57609-73-1) + 1-(2-deoxy-β-D-erythro-pentafuranosyl)-5-hydroxy-5-methyl-hydantoin (127707-34-0,38716-09-5) + (+)-cis-(5S,6R)-5,6-dihydroxy-5,6-dihydrothymidine (38709-52-3) + (-)-cis-(5R,6S)-6-hydroxy-5,6-dihydrothymidine (32926-52-6,68509-78-4)

Guidance literature:

In pyridine; water; at 60 ℃; for 3h;

DOI:10.1139/v85-002

Reference yield:

duplex AQ-5'-UUUUAAUUAAUUAAUUAAUAUAUUT-3'*3'-AAAATTAATTAATTAATTATATAAA-5', AQ = 2-anthraquinonecarboxamide-N-(2-ethyl) group → 8-oxo-7,8-dihydro-2'-deoxyguanosine (31077-24-4,62471-63-0) + 2'-deoxy-5-(hydroxymethyl)uridine (5116-24-5,15425-01-1,143156-50-7) + trans-5'-carboxy-5,6-dihydroxy-5,6-dihydro thymidine (38645-24-8) + (+)-cis-(5S,6R)-5,6-dihydroxy-5,6-dihydrothymidine (38709-52-3) + 5-formyl-2'-deoxyuridine (4494-26-2)

Guidance literature:

duplex AQ-5'-UUUUAAUUAAUUAAUUAAUAUAUUT-3'*3'-AAAATTAATTAATTAATTATATAAA-5', AQ = 2-anthraquinonecarboxamide-N-(2-ethyl) group; With air; at 30 ℃; for 0.25h; pH=7.0; Irradiation; aq. phosphate buffer;

Time; Mechanism; Reactivity; aq. buffer; Enzymatic reaction;

DOI:10.1039/b717437c

upstream raw materials:

(5R,6R)-trans-(+)-5-bromo-6-hydroxy-5,6-dihydrothymidine

thymidine

trans-(5S,6S)-6-hydroxy-5-(2,2,6,6-tetramethyl-4-oxo-1-piperidinyl-N-oxide)-5,6-dihydrothymidine

trans-(5R,6R)-6-hydroxy-5-(2,2,6,6-tetramethyl-4-oxo-1-piperidinyl-N-oxide)-5,6-dihydrothymidine