1,4-Anhydro-2-deoxy-3,5-bis-O-(t-butyldimethylsilyl)-D-erythro-pent-1-enitol

Base Information

• Chemical Name: 1,4-Anhydro-2-deoxy-3,5-bis-O-(t-butyldimethylsilyl)-D-erythro-pent-1-enitol
• CAS No.: 173327-56-5
• Molecular Formula: C17H36 O3 Si2
• Molecular Weight: 344.642
• European Community (EC) Number: 801-090-1
• DSSTox Substance ID: DTXSID80473894
• Nikkaji Number: J721.430H
• Wikidata: Q82303571
• Mol file: 173327-56-5.mol

Synonyms:173327-56-5;1,4-Anhydro-2-deoxy-3,5-bis-O-(t-butyldimethylsilyl)-D-erythro-pent-1-enitol;D-erythro-Pent-1-enitol, 1,4-anhydro-2-deoxy-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-;tert-butyl-[[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2,3-dihydrofuran-2-yl]methoxy]-dimethylsilane;1,4-Anhydro-3,5-bis-O-(tert-butyldimethylsilyl)2-deoxy-D-erythro-pent-1-enitol;3,5-Bis-O-(tert-butyldimethylsilyl)-D-ribal;DTXSID80473894;MFCD01630914;AKOS025294718;CS-15475;CS-0034718;C13531;1,4-Anhydro-3,5-bis-O-(tert-butyldimethylsilyl)2-deoxy-D-erythro-pent-1-enitol inverted exclamation mark-;tert-butyl(((2R,3S)-3-(tert-butyldimethylsilyloxy)-2,3-dihydrofuran-2-yl)methoxy)dimethylsilane

Chemical Property of 1,4-Anhydro-2-deoxy-3,5-bis-O-(t-butyldimethylsilyl)-D-erythro-pent-1-enitol

Chemical Property:

• Boiling Point: 336.6±42.0 °C(Predicted)
• PSA: 27.69000
• Density: 0.91±0.1 g/cm3(Predicted)
• LogP: 5.31110
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 344.22029807
• Heavy Atom Count: 22
• Complexity: 403

Purity/Quality:

99% ^*data from raw suppliers

3,5-Bis-O-(tert-butyldimethylsilyl)-D-ribal ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: R36/37/38:
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCC1C(C=CO1)O[Si](C)(C)C(C)(C)C
• Isomeric SMILES: CC(C)(C)[Si](C)(C)OC[C@@H]1[C@H](C=CO1)O[Si](C)(C)C(C)(C)C

Technology Process of 1,4-Anhydro-2-deoxy-3,5-bis-O-(t-butyldimethylsilyl)-D-erythro-pent-1-enitol

There total 11 articles about 1,4-Anhydro-2-deoxy-3,5-bis-O-(t-butyldimethylsilyl)-D-erythro-pent-1-enitol 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: 93.0%

3',5'-O-di(tert-butyldimethylsilyl)thymidine (40733-26-4) → 3,5-bis-O,O-(tert-butyldimethylsilyl)-1,2-didehydro-1,2-dideoxy-D-ribofuranose (173327-56-5)

Guidance literature:

With 2,6-dimethylpyridine; N,O-bis-(trimethylsilyl)-acetamide; bis(diphenylthiophosphinoyl)amine; In n-heptane; toluene; at 100 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.joc.1c00555

Reference yield: 65.0%

3,5-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-deoxy-D-ribose (90344-34-6) → 3,5-bis-O,O-(tert-butyldimethylsilyl)-1,2-didehydro-1,2-dideoxy-D-ribofuranose (173327-56-5)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; at -60 - 45 ℃; for 19h;

DOI:10.1021/jo0709504

Reference yield:

3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine (64911-18-8) → 3,5-bis-O,O-(tert-butyldimethylsilyl)-1,2-didehydro-1,2-dideoxy-D-ribofuranose (173327-56-5)

Guidance literature:

With ammonium sulfate; 2,6-di-tert-butyl-4-methyl-phenol; lithium hexamethyldisilazane; In n-heptane; at 140 ℃; for 34h; Inert atmosphere;

upstream raw materials:

3',5'-O-di(tert-butyldimethylsilyl)thymidine

3,5-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-deoxy-D-ribose

3,5-di-O-(tert-butyldimethylsilyl)-2-deoxy-D-ribono-1,4-lactone

D-2-deoxyribose

Downstream raw materials:

1-[(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydro-furan-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol

4-[(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydro-furan-2-yl]-4-hydroxy-cyclohexa-2,5-dienone

1-[(2R,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione