(3aR,4S,5S,5aS,6R,9aR,9bR)-2,2,4,5a,9,9-Hexamethyl-5-trityloxymethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5,6-triol

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Chemical Name:(3aR,4S,5S,5aS,6R,9aR,9bR)-2,2,4,5a,9,9-Hexamethyl-5-trityloxymethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5,6-triol
CAS No.:114299-57-9
Molecular Formula:C₃₇H₄₆O₆
Molecular Weight:586.769
Hs Code.:

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Chemical Property of (3aR,4S,5S,5aS,6R,9aR,9bR)-2,2,4,5a,9,9-Hexamethyl-5-trityloxymethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5,6-triol

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Technology Process of (3aR,4S,5S,5aS,6R,9aR,9bR)-2,2,4,5a,9,9-Hexamethyl-5-trityloxymethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5,6-triol

There total 20 articles about (3aR,4S,5S,5aS,6R,9aR,9bR)-2,2,4,5a,9,9-Hexamethyl-5-trityloxymethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5,6-triol 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: 83.0%

: 114273-64-2,125639-57-8
(3aR,5aS,6S,9aS,9bS)-2,2,4,5a,9,9-Hexamethyl-5-trityloxymethyl-3a,5a,6,7,8,9,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxol-6-ol

: 114299-57-9,125639-58-9
(3aR,4S,5S,5aS,6R,9aR,9bR)-2,2,4,5a,9,9-Hexamethyl-5-trityloxymethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5,6-triol

Guidance literature:: With osmium(VIII) oxide; hydrogen sulfide; 1.) pyridine, 20 deg C, 30 h, 2.) chloroform - dioxane, 23 deg C, 0.5 h;
DOI:10.1021/ja00219a058

Reference yield:

: 13051-32-6
dimethyl 2,2-dimethylglutarate

: 114299-57-9,125639-58-9
(3aR,4S,5S,5aS,6R,9aR,9bR)-2,2,4,5a,9,9-Hexamethyl-5-trityloxymethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5,6-triol

Guidance literature:: Multi-step reaction with 18 steps

3: tetrahydrofuran / 0.5 h / -78 °C

4: H₂, quinoline / Lindlar catalyst / benzene / 2 h / 25 °C

5: DMAP / CH₂Cl₂ / 2 h / Heating

6: 35 percent / Pd(PPh₃)4, Et₃N / tetrahydrofuran / 5 h / Heating

7: 25 percent / toluene / 5 h / 220 - 230 °C / in sealed tube

8: 90 percent / OsO₄, Me₃NO, pyridine / 2-methyl-propan-2-ol; H₂O / 18 h / Heating

9: 81 percent / SO₃-pyridine, Et₃N / 20 h / 20 °C

10: 85 percent / NaTeH / ethanol / 0.5 h / 23 °C

11: 87 percent / t-BuNH₃-BH₃ / methanol / 21 h / 23 °C

12: 95 percent / TsOH / benzene / 1 h / 23 °C

13: 94 percent / MCPBA / CH₂Cl₂ / 0.5 h / -25 °C

14: 68 percent / CaCO₃ / toluene / 70 h / Heating

15: 92 percent / LiOMe / tetrahydrofuran / 72 h / 23 °C

16: 89 percent / LiAlH₄ / diethyl ether / 1 h / Heating

17: 90 percent / DMAP / 1,2-dichloro-ethane / 6 h / Heating

18: 83 percent / 1.) OsO₄, 2.) H₂S / 1.) pyridine, 20 deg C, 30 h, 2.) chloroform - dioxane, 23 deg C, 0.5 h

With pyridine; quinoline; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogen telluride; pyridine-SO₃ complex; trimethylamine-N-oxide; N-tert-butylaminoborane; hydrogen sulfide; lithium methanolate; hydrogen; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; Lindlar's catalyst; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/ja00219a058

Reference yield:

: 141424-11-5
4,4-dimethyl-5-(tetrahydro-2H-pyran-2-yloxy)pentanal

: 114299-57-9,125639-58-9
(3aR,4S,5S,5aS,6R,9aR,9bR)-2,2,4,5a,9,9-Hexamethyl-5-trityloxymethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5,6-triol

Guidance literature:: Multi-step reaction with 17 steps

2: tetrahydrofuran / 0.5 h / -78 °C

3: H₂, quinoline / Lindlar catalyst / benzene / 2 h / 25 °C

4: DMAP / CH₂Cl₂ / 2 h / Heating

5: 35 percent / Pd(PPh₃)4, Et₃N / tetrahydrofuran / 5 h / Heating

6: 25 percent / toluene / 5 h / 220 - 230 °C / in sealed tube

7: 90 percent / OsO₄, Me₃NO, pyridine / 2-methyl-propan-2-ol; H₂O / 18 h / Heating

8: 81 percent / SO₃-pyridine, Et₃N / 20 h / 20 °C

9: 85 percent / NaTeH / ethanol / 0.5 h / 23 °C

10: 87 percent / t-BuNH₃-BH₃ / methanol / 21 h / 23 °C

11: 95 percent / TsOH / benzene / 1 h / 23 °C

12: 94 percent / MCPBA / CH₂Cl₂ / 0.5 h / -25 °C

13: 68 percent / CaCO₃ / toluene / 70 h / Heating

14: 92 percent / LiOMe / tetrahydrofuran / 72 h / 23 °C

15: 89 percent / LiAlH₄ / diethyl ether / 1 h / Heating

16: 90 percent / DMAP / 1,2-dichloro-ethane / 6 h / Heating

17: 83 percent / 1.) OsO₄, 2.) H₂S / 1.) pyridine, 20 deg C, 30 h, 2.) chloroform - dioxane, 23 deg C, 0.5 h

With pyridine; quinoline; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogen telluride; pyridine-SO₃ complex; trimethylamine-N-oxide; N-tert-butylaminoborane; hydrogen sulfide; lithium methanolate; hydrogen; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; Lindlar's catalyst; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/ja00219a058