(+)-(1'S,2R,5R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(1',2'-dihydroxyethyl)-1,3-oxathiolane

Base Information

• Chemical Name: (+)-(1'S,2R,5R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(1',2'-dihydroxyethyl)-1,3-oxathiolane
• CAS No.: 139757-71-4
• Molecular Formula: C₂₂H₃₀O₄SSi
• Molecular Weight: 418.629
• Mol file: 139757-71-4.mol

Synonyms:

Chemical Property of (+)-(1'S,2R,5R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(1',2'-dihydroxyethyl)-1,3-oxathiolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1'S,2R,5R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(1',2'-dihydroxyethyl)-1,3-oxathiolane

There total 19 articles about (+)-(1'S,2R,5R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(1',2'-dihydroxyethyl)-1,3-oxathiolane 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:

tert-Butyl-[(2R,5R)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-[1,3]oxathiolan-2-ylmethoxy]-diphenyl-silane (1025959-81-2) → (+)-(1'S,2R,5R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(1',2'-dihydroxyethyl)-1,3-oxathiolane (139757-71-4)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 0.5h; Yield given; Ambient temperature;

DOI:10.1021/jm00054a001

Reference yield:

L-gulose (655-45-8) → (+)-(1'S,2R,5R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(1',2'-dihydroxyethyl)-1,3-oxathiolane (139757-71-4)

Guidance literature:

Multi-step reaction with 10 steps

1: pyridine / 4 h / Ambient temperature

2: pyridine / 4 h / Ambient temperature

3: 99 percent / HBr / acetic acid / 15.5 h / 0 - 20 °C

4: potassium O-ethyl xanthate / acetone / 3 h / Heating

5: conc. NH₄OH / methanol

6: aq. NaIO₄ / methanol / 0.17 h / 0 °C

7: NaBH₄ / methanol; H₂O / 0.17 h / 0 °C

8: p-TsOH*H₂O / 1 h / Ambient temperature

9: imidazole / dimethylformamide / 1 h / Ambient temperature

10: p-TsOH*H₂O / methanol / 0.5 h / Ambient temperature

With pyridine; 1H-imidazole; ammonium hydroxide; sodium tetrahydroborate; sodium periodate; hydrogen bromide; potassium ethyl xanthogenate; toluene-4-sulfonic acid; In pyridine; methanol; water; acetic acid; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00054a001

Reference yield:

Toluene-4-sulfonic acid (2S,3S,4S,5S)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester (6619-07-4,26391-80-0,121363-57-3,121363-64-2,121363-65-3,121363-70-0) → (+)-(1'S,2R,5R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(1',2'-dihydroxyethyl)-1,3-oxathiolane (139757-71-4)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine / 4 h / Ambient temperature

2: 99 percent / HBr / acetic acid / 15.5 h / 0 - 20 °C

3: potassium O-ethyl xanthate / acetone / 3 h / Heating

4: conc. NH₄OH / methanol

5: aq. NaIO₄ / methanol / 0.17 h / 0 °C

6: NaBH₄ / methanol; H₂O / 0.17 h / 0 °C

7: p-TsOH*H₂O / 1 h / Ambient temperature

8: imidazole / dimethylformamide / 1 h / Ambient temperature

9: p-TsOH*H₂O / methanol / 0.5 h / Ambient temperature

With 1H-imidazole; ammonium hydroxide; sodium tetrahydroborate; sodium periodate; hydrogen bromide; potassium ethyl xanthogenate; toluene-4-sulfonic acid; In pyridine; methanol; water; acetic acid; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00054a001

upstream raw materials:

L-gulose

[(2R,5R)-5-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-[1,3]oxathiolan-2-yl]-methanol

(-)-1,6-dideoxy-1,6-thioanhydro-L-gulose

2,3,4-Tri-O-acetyl-1,6-thioanhydro-L-gulose

Downstream raw materials:

(2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carbaldehyde

(+)-(2R,5R)-5-iodo-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine

(-)-(2R,5S)-5-iodo-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine

(+)-(2R,5R)-5-bromo-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine