(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

Base Information

Chemical Name:(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
CAS No.:143169-68-0
Molecular Formula:C₃₀H₄₀O₅Si
Molecular Weight:508.73
Hs Code.:

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Chemical Property of (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

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Technology Process of (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

There total 35 articles about (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 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:

: 18427-19-5
1,2;5,6-di-O-isopropylidene-3-(2-hydroxyethyl)-α-D-allofuranoside

: 143169-68-0
(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

Guidance literature:: Multi-step reaction with 13 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

12: 688 mg / PCC, molecular sieves 4A / CH₂Cl₂ / 4 h

13: 698 mg / NaOMe / methanol / 21 h

With pyridine; 1H-imidazole; dmap; sodium hydroxide; sodium periodate; borane-THF; 4 A molecular sieve; potassium tert-butylate; hydrogen; dihydrogen peroxide; sodium methylate; 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:

: 113918-87-9
(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

: 143169-68-0
(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

Guidance literature:: Multi-step reaction with 13 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

12: 688 mg / PCC, molecular sieves 4A / CH₂Cl₂ / 4 h

13: 698 mg / NaOMe / methanol / 21 h

With 1H-imidazole; sodium hydroxide; sodium periodate; borane-THF; oxalyl dichloride; 4 A molecular sieve; hydrogen; dihydrogen peroxide; sodium methylate; 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:

: 143135-46-0,143135-47-1
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

: 143169-68-0
(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

Guidance literature:: Multi-step reaction with 9 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

8: 688 mg / PCC, molecular sieves 4A / CH₂Cl₂ / 4 h

9: 698 mg / NaOMe / methanol / 21 h

With 1H-imidazole; oxalyl dichloride; 4 A molecular sieve; hydrogen; sodium methylate; 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; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4020(01)80440-3