(2S,5S,2'S,5'S,2''S,5''S)-5-<5'-<5''-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2''-yl>tetrahydrofuran-2'-yl>tetrahydrofuran-2-methanol

Base Information

• Chemical Name: (2S,5S,2'S,5'S,2''S,5''S)-5-<5'-<5''-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2''-yl>tetrahydrofuran-2'-yl>tetrahydrofuran-2-methanol
• CAS No.: 149099-19-4
• Molecular Formula: C₃₀H₄₂O₅Si
• Molecular Weight: 510.746
• Mol file: 149099-19-4.mol

Synonyms:(2S,5S,2'S,5'S,2''S,5''S)-5-<5'-<5''-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2''-yl>tetrahydrofuran-2'-yl>tetrahydrofuran-2-methanol

Chemical Property of (2S,5S,2'S,5'S,2''S,5''S)-5-<5'-<5''-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2''-yl>tetrahydrofuran-2'-yl>tetrahydrofuran-2-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S,2'S,5'S,2''S,5''S)-5-<5'-<5''-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2''-yl>tetrahydrofuran-2'-yl>tetrahydrofuran-2-methanol

There total 16 articles about (2S,5S,2'S,5'S,2''S,5''S)-5-<5'-<5''-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2''-yl>tetrahydrofuran-2'-yl>tetrahydrofuran-2-methanol 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:

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one (102717-29-3) → (2S,5S,2'S,5'S,2''S,5''S)-5-<5'-<5''-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2''-yl>tetrahydrofuran-2'-yl>tetrahydrofuran-2-methanol (149099-19-4)

Guidance literature:

Multi-step reaction with 16 steps

1: 94 percent / DIBAH / toluene / 0.25 h / -78 °C

2: 90 percent / Et₃N / CH₂Cl₂ / 12 h / Ambient temperature

3: 61 percent / BF₃*Et₂O / acetonitrile / 0.17 h / -35 °C

4: 92 percent / NaOMe / 1.5 h / Ambient temperature

5: 86 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

6: 1.) Mg, CuBr*Me₂S / 1.) Et₂O, r.t., 1 h; -78 to -30 deg C, 30 min, 2.) -78 deg C to r.t., overnight

7: 92 percent / aq. AcOH / tetrahydrofuran / 48 h / Ambient temperature

8: pyridine / CH₂Cl₂ / 20 h / 0 °C

9: K₂CO₃ / methanol / 2 h / Ambient temperature

10: AcOH / CH₂Cl₂ / 2 h / Ambient temperature

11: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 to 0 deg C, 30 min

12: 1.) Mg, CuBr*Me₂S / 1.) Et₂O, r.t., 1 h; -78 to -30 deg C, 30 min, 2.) -78 deg C to r.t., overnight

13: aq. AcOH / 22 h / Ambient temperature

14: pyridine / CH₂Cl₂ / 11 h / 0 °C

15: K₂CO₃ / methanol / 3 h / Ambient temperature

16: AcOH / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; sodium methylate; diisobutylaluminium hydride; potassium carbonate; magnesium; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; acetonitrile;

Reference yield:

(2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol (201472-26-6) → (2S,5S,2'S,5'S,2''S,5''S)-5-<5'-<5''-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2''-yl>tetrahydrofuran-2'-yl>tetrahydrofuran-2-methanol (149099-19-4)

Guidance literature:

Multi-step reaction with 15 steps

1: 90 percent / Et₃N / CH₂Cl₂ / 12 h / Ambient temperature

2: 61 percent / BF₃*Et₂O / acetonitrile / 0.17 h / -35 °C

3: 92 percent / NaOMe / 1.5 h / Ambient temperature

4: 86 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

5: 1.) Mg, CuBr*Me₂S / 1.) Et₂O, r.t., 1 h; -78 to -30 deg C, 30 min, 2.) -78 deg C to r.t., overnight

6: 92 percent / aq. AcOH / tetrahydrofuran / 48 h / Ambient temperature

7: pyridine / CH₂Cl₂ / 20 h / 0 °C

8: K₂CO₃ / methanol / 2 h / Ambient temperature

9: AcOH / CH₂Cl₂ / 2 h / Ambient temperature

10: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 to 0 deg C, 30 min

11: 1.) Mg, CuBr*Me₂S / 1.) Et₂O, r.t., 1 h; -78 to -30 deg C, 30 min, 2.) -78 deg C to r.t., overnight

12: aq. AcOH / 22 h / Ambient temperature

13: pyridine / CH₂Cl₂ / 11 h / 0 °C

14: K₂CO₃ / methanol / 3 h / Ambient temperature

15: AcOH / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; sodium methylate; diisobutylaluminium hydride; potassium carbonate; magnesium; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile;

Reference yield:

1-acetoxy-2,3-dideoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-D-glycero-pentofuranose (201536-71-2) → (2S,5S,2'S,5'S,2''S,5''S)-5-<5'-<5''-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2''-yl>tetrahydrofuran-2'-yl>tetrahydrofuran-2-methanol (149099-19-4)

Guidance literature:

Multi-step reaction with 14 steps

1: 61 percent / BF₃*Et₂O / acetonitrile / 0.17 h / -35 °C

2: 92 percent / NaOMe / 1.5 h / Ambient temperature

3: 86 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

4: 1.) Mg, CuBr*Me₂S / 1.) Et₂O, r.t., 1 h; -78 to -30 deg C, 30 min, 2.) -78 deg C to r.t., overnight

5: 92 percent / aq. AcOH / tetrahydrofuran / 48 h / Ambient temperature

6: pyridine / CH₂Cl₂ / 20 h / 0 °C

7: K₂CO₃ / methanol / 2 h / Ambient temperature

8: AcOH / CH₂Cl₂ / 2 h / Ambient temperature

9: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 to 0 deg C, 30 min

10: 1.) Mg, CuBr*Me₂S / 1.) Et₂O, r.t., 1 h; -78 to -30 deg C, 30 min, 2.) -78 deg C to r.t., overnight

11: aq. AcOH / 22 h / Ambient temperature

12: pyridine / CH₂Cl₂ / 11 h / 0 °C

13: K₂CO₃ / methanol / 3 h / Ambient temperature

14: AcOH / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; sodium methylate; diisobutylaluminium hydride; potassium carbonate; magnesium; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile;

upstream raw materials:

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

(2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol

1-acetoxy-2,3-dideoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-D-glycero-pentofuranose

(2S,5S)-5-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2-carboxaldehyde