[(1R,2S,3S,4R,5R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,5-dihydroxy-cyclohexyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(1R,2S,3S,4R,5R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,5-dihydroxy-cyclohexyl]-carbamic acid tert-butyl ester
• CAS No.: 700361-03-1
• Molecular Formula: C₂₄H₄₁NO₆Si
• Molecular Weight: 467.678
• Mol file: 700361-03-1.mol

Synonyms:[(1R,2S,3S,4R,5R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,5-dihydroxy-cyclohexyl]-carbamic acid tert-butyl ester

Chemical Property of [(1R,2S,3S,4R,5R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,5-dihydroxy-cyclohexyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,2S,3S,4R,5R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,5-dihydroxy-cyclohexyl]-carbamic acid tert-butyl ester

There total 9 articles about [(1R,2S,3S,4R,5R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,5-dihydroxy-cyclohexyl]-carbamic acid tert-butyl ester 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: 70.0%

[6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohex-3-enyl]-carbamic acid tert-butyl ester (700361-02-0) → [(1R,2S,3S,4R,5R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,5-dihydroxy-cyclohexyl]-carbamic acid tert-butyl ester (700361-03-1)

Guidance literature:

With ruthenium trichloride; sodium periodate; In water; ethyl acetate; acetonitrile; at 0 ℃; for 0.05h;

DOI:10.1016/j.tetlet.2004.03.051

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → [(1R,2S,3S,4R,5R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,5-dihydroxy-cyclohexyl]-carbamic acid tert-butyl ester (700361-03-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: NaBH₄ / methanol / 0.5 h / 0 °C

1.2: dioxane / 18 h / 20 °C

2.1: diethyl ether / 6 h / -78 - -45 °C

3.1: NaBH₄ / methanol / 0.5 h / 0 °C

4.1: 90 percent / NaH / dimethylformamide / 1 h / 0 °C

5.1: 67 percent / CAN; NaHCO₃ / acetonitrile; H₂O / 0.5 h / 20 °C

6.1: MeOTf / acetonitrile / 0.42 h / 20 °C

6.2: NaBH₄ / methanol / 0.17 h / 0 °C

6.3: 83 percent / CuCl₂*2H₂O; CuO / acetonitrile; H₂O / 0.25 h / 20 °C

7.1: 56 percent / tetrahydrofuran / 4 h / -78 °C

8.1: Grubbs' catalyst with monosubstituted imidazolidine ligand / CH₂Cl₂ / 2 h / 20 °C

9.1: Et₃N / CH₂Cl₂ / 2 h / 20 °C

10.1: 70 percent / RuCl₃; NaIO₄ / ethyl acetate; acetonitrile; H₂O / 0.05 h / 0 °C

With ruthenium trichloride; sodium tetrahydroborate; sodium periodate; ammonium cerium(IV) nitrate; sodium hydride; sodium hydrogencarbonate; triethylamine; methyl trifluoromethanesulfonate; Grubbs' catalyst with monosubstituted imidazolidine ligand; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 7.1: Grignard addition;

DOI:10.1016/j.tetlet.2004.03.051

Reference yield:

[(R)-1-((S)-1-Benzyloxy-2-oxo-ethyl)-but-3-enyl]-carbamic acid tert-butyl ester (700360-99-2) → [(1R,2S,3S,4R,5R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,5-dihydroxy-cyclohexyl]-carbamic acid tert-butyl ester (700361-03-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 56 percent / tetrahydrofuran / 4 h / -78 °C

2: Grubbs' catalyst with monosubstituted imidazolidine ligand / CH₂Cl₂ / 2 h / 20 °C

3: Et₃N / CH₂Cl₂ / 2 h / 20 °C

4: 70 percent / RuCl₃; NaIO₄ / ethyl acetate; acetonitrile; H₂O / 0.05 h / 0 °C

With ruthenium trichloride; sodium periodate; triethylamine; Grubbs' catalyst with monosubstituted imidazolidine ligand; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetonitrile; 1: Grignard addition;

DOI:10.1016/j.tetlet.2004.03.051

upstream raw materials:

[6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohex-3-enyl]-carbamic acid tert-butyl ester

di-tert-butyl dicarbonate

[(R)-1-((S)-1-Benzyloxy-2-oxo-ethyl)-but-3-enyl]-carbamic acid tert-butyl ester

2-[tert-butoxycarbonyl-(4-methoxy-benzyl)-amino]-pent-4-enoic acid methyl ester

Downstream raw materials:

[(3aR,5R,6S,7R,7aS)-6-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dioxo-hexahydro-2λ⁶-benzo[1,3,2]dioxathiol-5-yl]-carbamic acid tert-butyl ester