2-[2,2-Dimethoxy-eth-(Z)-ylidene]-malonic acid benzyl ester methyl ester

Base Information

• Chemical Name: 2-[2,2-Dimethoxy-eth-(Z)-ylidene]-malonic acid benzyl ester methyl ester
• CAS No.: 161681-84-1
• Molecular Formula: C₁₅H₁₈O₆
• Molecular Weight: 294.304
• Mol file: 161681-84-1.mol

Synonyms:2-[2,2-Dimethoxy-eth-(Z)-ylidene]-malonic acid benzyl ester methyl ester

Chemical Property of 2-[2,2-Dimethoxy-eth-(Z)-ylidene]-malonic acid benzyl ester methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[2,2-Dimethoxy-eth-(Z)-ylidene]-malonic acid benzyl ester methyl ester

There total 1 articles about 2-[2,2-Dimethoxy-eth-(Z)-ylidene]-malonic acid benzyl ester methyl ester 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: 82.0%

dimethoxyacetaldehyde (51673-84-8) + benzyl methyl malonate (52267-39-7) → 2-[2,2-Dimethoxy-eth-(Z)-ylidene]-malonic acid benzyl ester methyl ester (161681-84-1)

Guidance literature:

With piperidine; In toluene; Heating;

DOI:10.1016/0040-4039(96)01205-1

Reference yield:

2-[2,2-Dimethoxy-eth-(Z)-ylidene]-malonic acid benzyl ester methyl ester (161681-84-1) → Topotecan hydrochloride (119413-54-6,123949-07-5)

Guidance literature:

Multi-step reaction with 9 steps

1: LDA / tetrahydrofuran / -78 up to -20 deg C

2: H₂ / 5percent Pd/C / methanol

3: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et₃N / tetrahydrofuran

4: TFA / H₂O; toluene

5: DDQ

6: diisobutylaluminum hydride (DIBAH) / CH₂Cl₂

7: 1.) NaBH₄; 2.) aq. NaOH / 1.) MeOH

8: 72 percent / 48percent HBr

9: 91 percent / CH₂Cl₂; propan-1-ol

With sodium hydroxide; sodium tetrahydroborate; hydrogen bromide; hydrogen; diisobutylaluminium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; toluene;

DOI:10.1016/0040-4039(96)01205-1

Reference yield:

2-[2,2-Dimethoxy-eth-(Z)-ylidene]-malonic acid benzyl ester methyl ester (161681-84-1) → (S)-10-hydroxycamptothecin (19685-09-7,64439-81-2)

Guidance literature:

Multi-step reaction with 8 steps

1: LDA / tetrahydrofuran / -78 up to -20 deg C

2: H₂ / 5percent Pd/C / methanol

3: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et₃N / tetrahydrofuran

4: TFA / H₂O; toluene

5: DDQ

6: diisobutylaluminum hydride (DIBAH) / CH₂Cl₂

7: 1.) NaBH₄; 2.) aq. NaOH / 1.) MeOH

8: 72 percent / 48percent HBr

With sodium hydroxide; sodium tetrahydroborate; hydrogen bromide; hydrogen; diisobutylaluminium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; toluene;

DOI:10.1016/0040-4039(96)01205-1

upstream raw materials:

dimethoxyacetaldehyde

benzyl methyl malonate

Downstream raw materials:

(S)-10-hydroxycamptothecin

10-methoxycamptothecin

Topotecan hydrochloride

Refernces