Spirocyclohexane-1,2-1,3dioxino4,5,6-hiindolizin-8-ol, 9-(1,1-dimethylethyl)dimethylsilyloxyoctahydro-, 3aS-(3a.alpha.,8.beta.,9.beta.,9a.beta.,9b.alpha.)-

Base Information

• Chemical Name: Spirocyclohexane-1,2-1,3dioxino4,5,6-hiindolizin-8-ol, 9-(1,1-dimethylethyl)dimethylsilyloxyoctahydro-, 3aS-(3a.alpha.,8.beta.,9.beta.,9a.beta.,9b.alpha.)-
• CAS No.: 156257-98-6
• Molecular Formula: C₂₀H₃₇NO₄Si
• Molecular Weight: 383.604
• Mol file: 156257-98-6.mol

Synonyms:Spirocyclohexane-1,2-1,3dioxino4,5,6-hiindolizin-8-ol, 9-(1,1-dimethylethyl)dimethylsilyloxyoctahydro-, 3aS-(3a.alpha.,8.beta.,9.beta.,9a.beta.,9b.alpha.)-

Chemical Property of Spirocyclohexane-1,2-1,3dioxino4,5,6-hiindolizin-8-ol, 9-(1,1-dimethylethyl)dimethylsilyloxyoctahydro-, 3aS-(3a.alpha.,8.beta.,9.beta.,9a.beta.,9b.alpha.)-

Chemical Property:

• Boiling Point: 454.6±45.0 °C(Predicted)
• PKA: 13.76±0.40(Predicted)
• PSA: 51.16000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 3.20790

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Spirocyclohexane-1,2-1,3dioxino4,5,6-hiindolizin-8-ol, 9-(1,1-dimethylethyl)dimethylsilyloxyoctahydro-, 3aS-(3a.alpha.,8.beta.,9.beta.,9a.beta.,9b.alpha.)-

There total 6 articles about Spirocyclohexane-1,2-1,3dioxino4,5,6-hiindolizin-8-ol, 9-(1,1-dimethylethyl)dimethylsilyloxyoctahydro-, 3aS-(3a.alpha.,8.beta.,9.beta.,9a.beta.,9b.alpha.)- 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:

6-O-benzoylcastanospermine (121104-76-5) → 7-O-t-butyldimethylsilyl-1,8-O-cyclohexylidene-6-epicastanospermine (156257-98-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / camphorsulfonic acid, triethylorthoformate / dimethylformamide / 1 h / 80 °C

2: 100.6 percent / imidazole / dimethylformamide / 55 deg C, 2 h; 40 deg C, overnight

3: 47 percent / NaOMe / tetrahydrofuran; methanol / Heating

4: 1.) DMSO, oxalyl chloride, Et₃N; 2.) NaBH₄ / 1.)CH₂Cl₂, -30 deg C, 20 min; 2.) EtOH, -30 deg C -> r.t.

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; sodium methylate; dimethyl sulfoxide; triethylamine; orthoformic acid triethyl ester; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)85075-4

Reference yield:

(1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine (79831-76-8) → 7-O-t-butyldimethylsilyl-1,8-O-cyclohexylidene-6-epicastanospermine (156257-98-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) (Bu₃Sn)2O / 1.) toluene, reflux, 2 h; 2.) 0 deg C, overnight

2: 74 percent / camphorsulfonic acid, triethylorthoformate / dimethylformamide / 1 h / 80 °C

3: 100.6 percent / imidazole / dimethylformamide / 55 deg C, 2 h; 40 deg C, overnight

4: 47 percent / NaOMe / tetrahydrofuran; methanol / Heating

5: 1.) DMSO, oxalyl chloride, Et₃N; 2.) NaBH₄ / 1.)CH₂Cl₂, -30 deg C, 20 min; 2.) EtOH, -30 deg C -> r.t.

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; sodium methylate; dimethyl sulfoxide; triethylamine; orthoformic acid triethyl ester; bis(tri-n-butyltin)oxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)85075-4

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 7-O-t-butyldimethylsilyl-1,8-O-cyclohexylidene-6-epicastanospermine (156257-98-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / camphorsulfonic acid, triethylorthoformate / dimethylformamide / 1 h / 80 °C

2: 100.6 percent / imidazole / dimethylformamide / 55 deg C, 2 h; 40 deg C, overnight

3: 47 percent / NaOMe / tetrahydrofuran; methanol / Heating

4: 1.) DMSO, oxalyl chloride, Et₃N; 2.) NaBH₄ / 1.)CH₂Cl₂, -30 deg C, 20 min; 2.) EtOH, -30 deg C -> r.t.

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; sodium methylate; dimethyl sulfoxide; triethylamine; orthoformic acid triethyl ester; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)85075-4

upstream raw materials:

7-O-t-butyldimethylsilyl-1,8-O-cyclohexylidenecastanospermine

6-O-benzoylcastanospermine

(1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine

cyclohexanone

Downstream raw materials:

6-epi-castanospermine