2-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.0^3,7]dodec-4-yl]ethanal

Base Information

• Chemical Name: 2-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.0^3,7]dodec-4-yl]ethanal
• CAS No.: 693251-12-6
• Molecular Formula: C₂₉H₃₈O₅SSi
• Molecular Weight: 526.769

Synonyms:2-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.0^3,7]dodec-4-yl]ethanal

Chemical Property of 2-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.0^3,7]dodec-4-yl]ethanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of 2-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.0^3,7]dodec-4-yl]ethanal

There total 1 articles about 2-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.0^3,7]dodec-4-yl]ethanal 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: 90.0%

2-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.03,7]dodec-4-yl]ethan-1-ol (667421-98-9) → 2-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.03,7]dodec-4-yl]ethanal (693251-12-6)

Guidance literature:

With pyridine-SO₃ complex; dimethyl sulfoxide; triethylamine; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

2-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.03,7]dodec-4-yl]ethanal (693251-12-6) → [(2R,11S,12R,14S,15R,17R,19S)-19-tert-butyldiphenylsiloxymethyl-15-methyl-13,18-dioxadispiro(2H-3,6-dihydropyran-6,5'-oxolane-2',3''-bicyclo[4.3.0]nonane)-2-yl]phenylmethoxymethane (693251-09-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.67 h / 0 °C

1.2: 46.4 mg / hexane; tetrahydrofuran / 0.33 h / -78 °C

2.1: 36.2 mg / H₂ / Lindlar catalyst / benzene / 7 h / 20 °C

3.1: 33.7 mg / DMSO; i-Pr₂NEt; SO₃*Py / CH₂Cl₂ / 0.25 h / 20 °C

4.1: 57 percent / Yb(OTf)3 / acetonitrile / 2 h / 20 °C

5.1: 72 percent / Raney Ni W-4 / ethanol / 1 h / Heating

With n-butyllithium; pyridine-SO₃ complex; Raney Ni W-4; hydrogen; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; ytterbium(III) triflate; Lindlar's catalyst; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetonitrile; benzene; 2.1: Lindlar reduction;

Reference yield:

2-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.03,7]dodec-4-yl]ethanal (693251-12-6) → [(1S,3S,5R,7S,9R,11R,14R,19R)-19-phenylmethoxymethyl-2,4,8,16-tetraoxa-13-thiapentacyclo[14.1.5.03,11.03,14.05,9]icos-19-en-7-yl]tert-butyldiphenylsiloxymethane (693251-10-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.67 h / 0 °C

1.2: 46.4 mg / hexane; tetrahydrofuran / 0.33 h / -78 °C

2.1: 36.2 mg / H₂ / Lindlar catalyst / benzene / 7 h / 20 °C

3.1: 33.7 mg / DMSO; i-Pr₂NEt; SO₃*Py / CH₂Cl₂ / 0.25 h / 20 °C

4.1: 57 percent / Yb(OTf)3 / acetonitrile / 2 h / 20 °C

With n-butyllithium; pyridine-SO₃ complex; hydrogen; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; ytterbium(III) triflate; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; benzene; 2.1: Lindlar reduction;

upstream raw materials:

2-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.0^3,7]dodec-4-yl]ethan-1-ol

Downstream raw materials:

[(2R,11S,12R,14S,15R,17R,19S)-19-tert-butyldiphenylsiloxymethyl-15-methyl-13,18-dioxadispiro(2H-3,6-dihydropyran-6,5'-oxolane-2',3''-bicyclo[4.3.0]nonane)-2-yl]phenylmethoxymethane

[(1S,3S,5R,7S,9R,11R,14R,19R)-19-phenylmethoxymethyl-2,4,8,16-tetraoxa-13-thiapentacyclo[14.1.5.0^3,11.0^3,14.0^5,9]icos-19-en-7-yl]tert-butyldiphenylsiloxymethane

(6R)-1-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.0^3,7]dodec-4-yl](3Z)-6-triethylsiloxy-7-phenylmethoxyhept-3-en-2-one

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