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

Base Information

• Chemical Name: (2S,5S,1'S)-2-<1'-(Benzyloxy)-3'-(phenylthio)propyl>-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran
• CAS No.: 170305-64-3
• Molecular Formula: C₃₇H₄₄O₃SSi
• Molecular Weight: 596.906
• Mol file: 170305-64-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (2S,5S,1'S)-2-<1'-(Benzyloxy)-3'-(phenylthio)propyl>-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran 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: 97.0%

diphenyldisulfane (882-33-7) + (γS,2S,5S)-γ-(Benzyloxy)-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2-propanol (170305-58-5) → (2S,5S,1'S)-2-<1'-(Benzyloxy)-3'-(phenylthio)propyl>-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran (170305-64-3)

Guidance literature:

With pyridine; tributylphosphine; In dichloromethane; for 1h; Ambient temperature;

Reference yield:

(2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol (201472-26-6) → (2S,5S,1'S)-2-<1'-(Benzyloxy)-3'-(phenylthio)propyl>-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran (170305-64-3)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; sodium tetrahydroborate; tributylphosphine; boron trifluoride diethyl etherate; oxygen; sodium methylate; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; ozone; triethylamine; triphenylphosphine; 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,1'S)-2-<1'-(Benzyloxy)-3'-(phenylthio)propyl>-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran (170305-64-3)

Guidance literature:

Multi-step reaction with 8 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

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

upstream raw materials:

diphenyldisulfane

(γS,2S,5S)-γ-(Benzyloxy)-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2-propanol

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

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

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

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