(3aS,7S)-dimethyl 8-((benzyloxy)methyl)-3,3a,6,7-tetrahydro-7-[(t-butyldimethylsiloxy)methyl]-4-methylazulene-2,2(1H)-dicarboxylate

Base Information

Chemical Name:(3aS,7S)-dimethyl 8-((benzyloxy)methyl)-3,3a,6,7-tetrahydro-7-[(t-butyldimethylsiloxy)methyl]-4-methylazulene-2,2(1H)-dicarboxylate
CAS No.:866825-12-9
Molecular Formula:C₃₀H₄₄O₆Si
Molecular Weight:528.761
Hs Code.:

Synonyms:(3aS,7S)-dimethyl 8-((benzyloxy)methyl)-3,3a,6,7-tetrahydro-7-[(t-butyldimethylsiloxy)methyl]-4-methylazulene-2,2(1H)-dicarboxylate

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Chemical Property of (3aS,7S)-dimethyl 8-((benzyloxy)methyl)-3,3a,6,7-tetrahydro-7-[(t-butyldimethylsiloxy)methyl]-4-methylazulene-2,2(1H)-dicarboxylate

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Technology Process of (3aS,7S)-dimethyl 8-((benzyloxy)methyl)-3,3a,6,7-tetrahydro-7-[(t-butyldimethylsiloxy)methyl]-4-methylazulene-2,2(1H)-dicarboxylate

There total 10 articles about (3aS,7S)-dimethyl 8-((benzyloxy)methyl)-3,3a,6,7-tetrahydro-7-[(t-butyldimethylsiloxy)methyl]-4-methylazulene-2,2(1H)-dicarboxylate 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:

: 866825-08-3
2-(4-benzyloxy-2-butynyl)malonic acid dimethyl ester

: 866825-12-9
(3aS,7S)-dimethyl 8-((benzyloxy)methyl)-3,3a,6,7-tetrahydro-7-[(t-butyldimethylsiloxy)methyl]-4-methylazulene-2,2(1H)-dicarboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: NaH / [Rh(CO)2Cl]2 / tetrahydrofuran

2: oxalyl chloride; N,N-dimethylformamide / CH₂Cl₂ / 3 h / 20 °C

3: LiAlH(OtBu)3 / tetrahydrofuran / 1 h / -78 °C

4: [Rh(CO)2Cl]2 / toluene / 0.5 h / 110 °C

5: NaBH₄ / tetrahydrofuran / 1.25 h / 0 °C

6: imidazole / dimethylformamide / 4 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; sodium hydride; lithium tri-t-butoxyaluminum hydride; N,N-dimethyl-formamide; di(rhodium)tetracarbonyl dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2006.05.087

Reference yield:

: 91142-50-6
4-benzyloxy-2-butyn-1-ol

: 866825-12-9
(3aS,7S)-dimethyl 8-((benzyloxy)methyl)-3,3a,6,7-tetrahydro-7-[(t-butyldimethylsiloxy)methyl]-4-methylazulene-2,2(1H)-dicarboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 92 percent / triethylamine / CH₂Cl₂

2.1: NaH / tetrahydrofuran / 0.42 h / 0 °C

2.2: 97 percent / tetrahydrofuran / 2.5 h / 20 °C

3.1: NaH / [Rh(CO)2Cl]2 / tetrahydrofuran

4.1: oxalyl chloride; N,N-dimethylformamide / CH₂Cl₂ / 3 h / 20 °C

5.1: LiAlH(OtBu)3 / tetrahydrofuran / 1 h / -78 °C

6.1: [Rh(CO)2Cl]2 / toluene / 0.5 h / 110 °C

7.1: NaBH₄ / tetrahydrofuran / 1.25 h / 0 °C

8.1: imidazole / dimethylformamide / 4 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; sodium hydride; lithium tri-t-butoxyaluminum hydride; triethylamine; N,N-dimethyl-formamide; di(rhodium)tetracarbonyl dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2006.05.087

Reference yield:

: 214978-16-2
4-(benzyloxy)but-2-ynyl methanesulfonate

: 866825-12-9
(3aS,7S)-dimethyl 8-((benzyloxy)methyl)-3,3a,6,7-tetrahydro-7-[(t-butyldimethylsiloxy)methyl]-4-methylazulene-2,2(1H)-dicarboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / tetrahydrofuran / 0.42 h / 0 °C

1.2: 97 percent / tetrahydrofuran / 2.5 h / 20 °C

2.1: NaH / [Rh(CO)2Cl]2 / tetrahydrofuran

3.1: oxalyl chloride; N,N-dimethylformamide / CH₂Cl₂ / 3 h / 20 °C

4.1: LiAlH(OtBu)3 / tetrahydrofuran / 1 h / -78 °C

5.1: [Rh(CO)2Cl]2 / toluene / 0.5 h / 110 °C

6.1: NaBH₄ / tetrahydrofuran / 1.25 h / 0 °C

7.1: imidazole / dimethylformamide / 4 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; sodium hydride; lithium tri-t-butoxyaluminum hydride; N,N-dimethyl-formamide; di(rhodium)tetracarbonyl dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2006.05.087