(3aR,4S,5S,5aS,6R,9aR,9bR)-5-Hydroxymethyl-6-(4-methoxy-benzyloxy)-2,2,4,5a,9,9-hexamethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5-diol

Base Information

• Chemical Name: (3aR,4S,5S,5aS,6R,9aR,9bR)-5-Hydroxymethyl-6-(4-methoxy-benzyloxy)-2,2,4,5a,9,9-hexamethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5-diol
• CAS No.: 114273-82-4
• Molecular Formula: C₂₆H₄₀O₇
• Molecular Weight: 464.599

Synonyms:(3aR,4S,5S,5aS,6R,9aR,9bR)-5-Hydroxymethyl-6-(4-methoxy-benzyloxy)-2,2,4,5a,9,9-hexamethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5-diol

Chemical Property of (3aR,4S,5S,5aS,6R,9aR,9bR)-5-Hydroxymethyl-6-(4-methoxy-benzyloxy)-2,2,4,5a,9,9-hexamethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (3aR,4S,5S,5aS,6R,9aR,9bR)-5-Hydroxymethyl-6-(4-methoxy-benzyloxy)-2,2,4,5a,9,9-hexamethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5-diol

There total 22 articles about (3aR,4S,5S,5aS,6R,9aR,9bR)-5-Hydroxymethyl-6-(4-methoxy-benzyloxy)-2,2,4,5a,9,9-hexamethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5-diol 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%

(3aR,4S,5S,5aS,6R,9aR,9bR)-6-(4-Methoxy-benzyloxy)-2,2,4,5a,9,9-hexamethyl-5-trityloxymethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5-diol (114273-65-3,125639-59-0) → (3aR,4S,5S,5aS,6R,9aR,9bR)-5-Hydroxymethyl-6-(4-methoxy-benzyloxy)-2,2,4,5a,9,9-hexamethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5-diol (114273-82-4)

Guidance literature:

toluene-4-sulfonic acid; In methanol; chloroform; at 20 ℃; for 0.666667h;

DOI:10.1021/ja00219a058

Reference yield:

dimethyl 2,2-dimethylglutarate (13051-32-6) → (3aR,4S,5S,5aS,6R,9aR,9bR)-5-Hydroxymethyl-6-(4-methoxy-benzyloxy)-2,2,4,5a,9,9-hexamethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5-diol (114273-82-4)

Guidance literature:

Multi-step reaction with 20 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

19: 91 percent / NaH / hexamethylphosphoric acid triamide; tetrahydrofuran / 3 h / 23 °C

20: 95 percent / TsOH / CHCl₃; methanol / 0.67 h / 20 °C

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; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; Lindlar's catalyst; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; chloroform; water; 1,2-dichloro-ethane; toluene; tert-butyl alcohol; benzene;

DOI:10.1021/ja00219a058

Reference yield:

4,4-dimethyl-5-(tetrahydro-2H-pyran-2-yloxy)pentanal (141424-11-5) → (3aR,4S,5S,5aS,6R,9aR,9bR)-5-Hydroxymethyl-6-(4-methoxy-benzyloxy)-2,2,4,5a,9,9-hexamethyl-decahydro-naphtho[1,2-d][1,3]dioxole-4,5-diol (114273-82-4)

Guidance literature:

Multi-step reaction with 19 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

18: 91 percent / NaH / hexamethylphosphoric acid triamide; tetrahydrofuran / 3 h / 23 °C

19: 95 percent / TsOH / CHCl₃; methanol / 0.67 h / 20 °C

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; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; Lindlar's catalyst; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; chloroform; water; 1,2-dichloro-ethane; toluene; tert-butyl alcohol; benzene;

DOI:10.1021/ja00219a058

upstream raw materials:

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

dimethyl 2,2-dimethylglutarate

(3aβ,5aβ,6aα,9aα,9bα,9cβ)-Decahydro-1,1,8,8,9c-pentamethyl-6-methylene-5H-furo<4',3',2':4,5>naphtho<1,2-d><1,3>dioxol-5-one

(3aβ,,6aα,9aα,9bβ,9cβ)-1,2,3,3a,6a,9a,9b,9c-Octahydro-1,1,6,8,8,9c-hexamethyl-5H-furo<4',3',2':4,5>naphtho<1,2-d><1,3>dioxol-5-one

Downstream raw materials:

C₂₈H₄₂O₈

C₂₈H₄₀O₈

(3aR,3bS,5S,7aR,7bS,8R,11aR,11bR)-7a-Hydroxy-8-(4-methoxy-benzyloxy)-2,2,3b,5,7b,11,11-heptamethyl-5-vinyl-dodecahydro-1,3,4-trioxa-cyclopenta[l]phenanthren-7-one

C₃₀H₄₄O₉

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