(3S,2'S,5'S)-3-(Benzyloxy)-3-<5'-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>propyl phenyl sulfone

Base Information

• Chemical Name: (3S,2'S,5'S)-3-(Benzyloxy)-3-<5'-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>propyl phenyl sulfone
• CAS No.: 170305-59-6
• Molecular Formula: C₃₇H₄₄O₅SSi
• Molecular Weight: 628.905
• Mol file: 170305-59-6.mol

Synonyms:(3S,2'S,5'S)-3-(Benzyloxy)-3-<5'-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>propyl phenyl sulfone

Chemical Property of (3S,2'S,5'S)-3-(Benzyloxy)-3-<5'-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>propyl phenyl sulfone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,2'S,5'S)-3-(Benzyloxy)-3-<5'-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>propyl phenyl sulfone

There total 10 articles about (3S,2'S,5'S)-3-(Benzyloxy)-3-<5'-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>propyl phenyl sulfone 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: 98.0%

(2S,5S,1'S)-2-<1'-(Benzyloxy)-3'-(phenylthio)propyl>-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran (170305-64-3) → (3S,2'S,5'S)-3-(Benzyloxy)-3-<5'-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>propyl phenyl sulfone (170305-59-6)

Guidance literature:

With magnesium monoperoxyphthalate hexahydrate; In ethanol; for 0.5h; Ambient temperature;

Reference yield:

(2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol (201472-26-6) → (3S,2'S,5'S)-3-(Benzyloxy)-3-<5'-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>propyl phenyl sulfone (170305-59-6)

Guidance literature:

Multi-step reaction with 10 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: 93 percent / SnCl₄ / CH₂Cl₂ / 1.) -78 deg C, 3 min, 2.) -78 deg C, 5 min

6: 91 percent / NaH / tetrahydrofuran / 1.) 15 min, 2.) r.t., 12 h

7: 1.) O₃, O₂, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C to r.t., 1 h

8: 91 percent / NaBH₄ / methanol / 0.5 h

9: 97 percent / pyridine, Bu₃P / CH₂Cl₂ / 1 h / Ambient temperature

10: 98 percent / magnesium monoperoxophthalate / ethanol / 0.5 h / Ambient temperature

With pyridine; sodium tetrahydroborate; tributylphosphine; boron trifluoride diethyl etherate; oxygen; sodium methylate; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; magnesium monoperoxyphthalate hexahydrate; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; acetonitrile;

Reference yield:

1-acetoxy-2,3-dideoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-D-glycero-pentofuranose (201536-71-2) → (3S,2'S,5'S)-3-(Benzyloxy)-3-<5'-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>propyl phenyl sulfone (170305-59-6)

Guidance literature:

Multi-step reaction with 9 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: 93 percent / SnCl₄ / CH₂Cl₂ / 1.) -78 deg C, 3 min, 2.) -78 deg C, 5 min

5: 91 percent / NaH / tetrahydrofuran / 1.) 15 min, 2.) r.t., 12 h

6: 1.) O₃, O₂, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C to r.t., 1 h

7: 91 percent / NaBH₄ / methanol / 0.5 h

8: 97 percent / pyridine, Bu₃P / CH₂Cl₂ / 1 h / Ambient temperature

9: 98 percent / magnesium monoperoxophthalate / ethanol / 0.5 h / Ambient temperature

With pyridine; sodium tetrahydroborate; tributylphosphine; boron trifluoride diethyl etherate; oxygen; sodium methylate; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; magnesium monoperoxyphthalate hexahydrate; ozone; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; acetonitrile;

upstream raw materials:

(2S,5S,1'S)-2-<1'-(Benzyloxy)-3'-(phenylthio)propyl>-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran

(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

Downstream raw materials:

(1R,4S,2'S,5'S)-4-(Benzyloxy)-1,4-bis<5'-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>butan-1-ol

(4S,2'S,5'S)-4-(Benzyloxy)-1,4-bis<5'-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>butanone