(1R,3R,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexane-1-carbaldehyde

Base Information

• Chemical Name: (1R,3R,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexane-1-carbaldehyde
• CAS No.: 128209-97-2
• Molecular Formula: C₁₄H₂₈O₃Si
• Molecular Weight: 272.46
• Mol file: 128209-97-2.mol

Synonyms:(1R,3R,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexane-1-carbaldehyde

Chemical Property of (1R,3R,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexane-1-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexane-1-carbaldehyde

There total 35 articles about (1R,3R,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexane-1-carbaldehyde 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: 95.0%

methyl (1R,3R,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexane-1-carboxylate (127604-97-1) → (1R,3R,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexane-1-carbaldehyde (128209-97-2)

Guidance literature:

With diisobutylaluminium hydride; In hexane; at -78 ℃; for 1.5h; Inert atmosphere;

Reference yield: 92.0%

((1R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-methoxycyclohexyl)methanol → (1R,3R,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexane-1-carbaldehyde (128209-97-2)

Guidance literature:

((1R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-methoxycyclohexyl)methanol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1.75h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 ℃; Inert atmosphere;

DOI:10.1002/chem.200801656

Reference yield:

(1R,2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexanol (148933-83-9) → (1R,3R,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexane-1-carbaldehyde (128209-97-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) r.t., 2 h

2: LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) 25 deg C, 2 h

3: Pd(OAc)2 / acetonitrile / 24 h / 50 °C

4: 95 percent / LiBH₄, CeCl₃*7H₂O / tetrahydrofuran; methanol / 1 h / -78 °C

5: 2.) LiEt₃BH / 1.) xylene, reflux, 48 h, 2.) THF, r.t., 2 h

6: 100 percent / H₂ / 10percent Pd/C / ethanol / 16 h / 25 °C

7: 1.) o-O₂NC₆H₄SeCN, n-Bu₃P, 2.) 30percent aq. H₂O₂ / 1.) THF, 25 deg C, 3 h, 2.) THF, 25 deg C, 6 h

8: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) 25 deg C, overnight

With palladium diacetate; lithium borohydride; ortho-nitrophenyl selenocyanate; cerium(III) chloride; oxalyl dichloride; dimethylsulfide; tributylphosphine; hydrogen; dihydrogen peroxide; lithium triethylborohydride; ozone; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; acetonitrile;

upstream raw materials:

methyl (1R,3R,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexane-1-carboxylate

2-[(1S,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-ethanol

(1R,2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexanol

(5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enone

Downstream raw materials:

(E)-(2S,3S)-5-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-3-methoxymethoxy-2,4-dimethyl-pent-4-enal

(E)-(2S,3S)-5-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-3-hydroxy-2,4-dimethyl-pent-4-enethioic acid S-phenyl ester

Acetic acid (E)-(3S,4R,5S)-7-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-3-hydroxy-5-methoxymethoxy-4,6-dimethyl-1-methylene-hept-6-enyl ester

(E)-(2S,3S)-5-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-3-methoxymethoxy-2,4-dimethyl-pent-4-enethioic acid S-phenyl ester

Refernces

• 1、 Haller, Bernd-Uwe,Kruber, Susanne,Maier, Martin E.. "A practical synthesis of the cyclohexyl part of the immunosuppressant FK506". experimental part. p. 656 - 661. Retrieved 2011/10/09.
• 2、 Kouklovsky,Ley,Marsden. "Studies towards the total synthesis of rapamycin: Preparation of the cyclohexyl C33-C42 fragment and further coupling to afford the C22-C42 carbon unit". . p. 2091 - 2094. Retrieved 2007/10/02.