(1R,3R,4S,5R,6S,8R,9R)-6-Hydroxy-4,11,11-trimethyl-5-<2-(tert-butyldiphenylsilyloxy)ethyl>-2,10,12-trioxatricyclo<7.3.0.0^3,8>dodecane

Base Information

• Chemical Name: (1R,3R,4S,5R,6S,8R,9R)-6-Hydroxy-4,11,11-trimethyl-5-<2-(tert-butyldiphenylsilyloxy)ethyl>-2,10,12-trioxatricyclo<7.3.0.0^3,8>dodecane
• CAS No.: 143169-66-8
• Molecular Formula: C₃₀H₄₂O₅Si
• Molecular Weight: 510.746

Synonyms:

Chemical Property of (1R,3R,4S,5R,6S,8R,9R)-6-Hydroxy-4,11,11-trimethyl-5-<2-(tert-butyldiphenylsilyloxy)ethyl>-2,10,12-trioxatricyclo<7.3.0.0^3,8>dodecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4S,5R,6S,8R,9R)-6-Hydroxy-4,11,11-trimethyl-5-<2-(tert-butyldiphenylsilyloxy)ethyl>-2,10,12-trioxatricyclo<7.3.0.0^3,8>dodecane

There total 22 articles about (1R,3R,4S,5R,6S,8R,9R)-6-Hydroxy-4,11,11-trimethyl-5-<2-(tert-butyldiphenylsilyloxy)ethyl>-2,10,12-trioxatricyclo<7.3.0.0^3,8>dodecane 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:

1,2;5,6-di-O-isopropylidene-3-(2-hydroxyethyl)-α-D-allofuranoside (18427-19-5) → (1R,3R,4S,5R,6S,8R,9R)-6-Hydroxy-4,11,11-trimethyl-5-<2-(tert-butyldiphenylsilyloxy)ethyl>-2,10,12-trioxatricyclo<7.3.0.03,8>dodecane (143169-66-8)

Guidance literature:

Multi-step reaction with 11 steps

1: PCC, molecular sieves 4A / CH₂Cl₂ / 0.75 h

2: 87 percent / tetrahydrofuran / 0.75 h / Ambient temperature

3: 1) BH₃*THF, 2) 35percent aq. H₂O₂, 3M aq. NaOH / 1) THF, 0 deg C, 3h, 2) water, 30 min

4: imidazole / dimethylformamide / 3 h

5: 64 percent / AcOH / tetrahydrofuran; H₂O / 15 h

6: 681 mg / NaIO₄ / methanol; H₂O / 1 h

7: 731 mg / tetrahydrofuran / 0.5 h / Heating

8: 558 mg / PCC, molecular sieves 4A / CH₂Cl₂ / 4 h

9: 31 percent / t-BuOK / benzene / 0.5 h / 0 °C

10: 80 percent / MeSO₂Cl, pyridine, 4-dimethylaminopyridine / 15 h / 70 °C

11: 25.5 percent / H₂ / Raney Ni T-4 / ethanol / 32 h / 2844.3 Torr

With pyridine; 1H-imidazole; dmap; sodium hydroxide; sodium periodate; borane-THF; 4 A molecular sieve; potassium tert-butylate; hydrogen; dihydrogen peroxide; acetic acid; methanesulfonyl chloride; pyridinium chlorochromate; Raney Ni T-4; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)80440-3

Reference yield:

(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]tetrahydrofuro[2,3-d][1,3]dioxole (113918-87-9) → (1R,3R,4S,5R,6S,8R,9R)-6-Hydroxy-4,11,11-trimethyl-5-<2-(tert-butyldiphenylsilyloxy)ethyl>-2,10,12-trioxatricyclo<7.3.0.03,8>dodecane (143169-66-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 16.10 g / 50percent aq. AcOH / 12 h

2: 14.90 g / NaIO₄ / methanol; H₂O / 0.67 h

3: tetrahydrofuran / 1 h / Ambient temperature

4: 1) BH₃*THF, 2) 30percent aq. H₂O₂, 3N aq. NaOH / 1) THF, 0 deg C, 4 h, 2) water, 40 min, r.t.

5: imidazole / dimethylformamide / 5.5 h

6: 85 percent / cyclohexene / 20percent Pd(OH)2/C / ethanol / 4 h / Heating

7: 1) (COCl)2, DMSO, 2) (i-Pr)2NEt / 1) CH₂Cl₂, -78 deg C, 2 h, 2) a) to r.t., b) r.t., 10 min

8: 3 percent / DBU / benzene / 33 h / Heating

9: tetrahydrofuran / 2 h / Ambient temperature

10: PCC, molecular sieves 4A / CH₂Cl₂ / 7.5 h

11: 25.5 percent / H₂ / Raney Ni T-4 / ethanol / 32 h / 2844.3 Torr

With 1H-imidazole; sodium hydroxide; sodium periodate; borane-THF; oxalyl dichloride; 4 A molecular sieve; hydrogen; dihydrogen peroxide; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; cyclohexene; palladium dihydroxide; Raney Ni T-4; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)80440-3

Reference yield:

1-[(3aR,5S,6R,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-butane-1,4-diol (143135-46-0,143135-47-1) → (1R,3R,4S,5R,6S,8R,9R)-6-Hydroxy-4,11,11-trimethyl-5-<2-(tert-butyldiphenylsilyloxy)ethyl>-2,10,12-trioxatricyclo<7.3.0.03,8>dodecane (143169-66-8)

Guidance literature:

Multi-step reaction with 7 steps

1: imidazole / dimethylformamide / 5.5 h

2: 85 percent / cyclohexene / 20percent Pd(OH)2/C / ethanol / 4 h / Heating

3: 1) (COCl)2, DMSO, 2) (i-Pr)2NEt / 1) CH₂Cl₂, -78 deg C, 2 h, 2) a) to r.t., b) r.t., 10 min

4: 3 percent / DBU / benzene / 33 h / Heating

5: tetrahydrofuran / 2 h / Ambient temperature

6: PCC, molecular sieves 4A / CH₂Cl₂ / 7.5 h

7: 25.5 percent / H₂ / Raney Ni T-4 / ethanol / 32 h / 2844.3 Torr

With 1H-imidazole; oxalyl dichloride; 4 A molecular sieve; hydrogen; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; cyclohexene; palladium dihydroxide; Raney Ni T-4; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)80440-3

upstream raw materials:

1,2;5,6-di-O-isopropylidene-3-(2-hydroxyethyl)-α-D-allofuranoside

(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]tetrahydrofuro[2,3-d][1,3]dioxole

5-[(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-pentane-1,4-diol

[(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-acetaldehyde

Downstream raw materials:

(1R,3R,4S,5S,6S,8R,9R)-6-Hydroxy-4,11,11-trimethyl-5-<2-(tert-butyldiphenylsilyloxy)ethyl>-2,10,12-trioxatricyclo<7.3.0.0^3,8>dodecane

(3aR,4aR,5S,6S,8aR,8bR)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2,5-trimethyl-hexahydro-benzo[4,5]furo[2,3-d][1,3]dioxol-7-one

(1R,3R,4S,5S,6S,8R,9R)-6-Hydroxy-4,11,11-trimethyl-5-<2-(tert-butyldiphenylsilyloxy)ethyl>-2,10,12-trioxatricyclo<7.3.0.0^3,8>dodecane 6-acetate

(3aR,4aR,5S,6R,8aR,8bR)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2,5-trimethyl-hexahydro-benzo[4,5]furo[2,3-d][1,3]dioxol-7-one

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