3-benzyloxy-estra-1,3,5⁽¹⁰⁾,16-tetraeno[17,16-e]-2'-(N-tert-butoxycarbonyl-glycyl-S-benzyl-L-cysteinylamino)pyrimidine

Base Information

• Chemical Name: 3-benzyloxy-estra-1,3,5⁽¹⁰⁾,16-tetraeno[17,16-e]-2'-(N-tert-butoxycarbonyl-glycyl-S-benzyl-L-cysteinylamino)pyrimidine
• CAS No.: 669056-36-4
• Molecular Formula: C₄₄H₅₁N₅O₅S
• Molecular Weight: 761.985

Synonyms:3-benzyloxy-estra-1,3,5⁽¹⁰⁾,16-tetraeno[17,16-e]-2'-(N-tert-butoxycarbonyl-glycyl-S-benzyl-L-cysteinylamino)pyrimidine

Chemical Property of 3-benzyloxy-estra-1,3,5⁽¹⁰⁾,16-tetraeno[17,16-e]-2'-(N-tert-butoxycarbonyl-glycyl-S-benzyl-L-cysteinylamino)pyrimidine

Chemical Property:

Purity/Quality:

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Technology Process of 3-benzyloxy-estra-1,3,5⁽¹⁰⁾,16-tetraeno[17,16-e]-2'-(N-tert-butoxycarbonyl-glycyl-S-benzyl-L-cysteinylamino)pyrimidine

There total 5 articles about 3-benzyloxy-estra-1,3,5⁽¹⁰⁾,16-tetraeno[17,16-e]-2'-(N-tert-butoxycarbonyl-glycyl-S-benzyl-L-cysteinylamino)pyrimidine 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: 61.0%

BOC-glycine (4530-20-5) + 3-benzyloxy-estra-1,3,5(10),16-tetraeno[17,16-e]-2'-(S-benzyl-L-cysteinylamino)pyrimidine (669056-35-3) → 3-benzyloxy-estra-1,3,5(10),16-tetraeno[17,16-e]-2'-(N-tert-butoxycarbonyl-glycyl-S-benzyl-L-cysteinylamino)pyrimidine (669056-36-4)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/S0039-128X(03)00145-4

Reference yield:

Estrone (53-16-7) → 3-benzyloxy-estra-1,3,5(10),16-tetraeno[17,16-e]-2'-(N-tert-butoxycarbonyl-glycyl-S-benzyl-L-cysteinylamino)pyrimidine (669056-36-4)

Guidance literature:

Multi-step reaction with 7 steps

1: NaH / dimethylformamide

2: 97 percent / sodium methoxide / toluene

3: 77 percent / benzene / Heating

4: 86 percent / NaOMe / propan-1-ol / 70 h / 80 - 90 °C

5: 43 percent / DCC / CH₂Cl₂ / 7 h / 20 °C

6: 95 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

7: 61 percent / DCC / CH₂Cl₂ / 4 h / 20 °C

With sodium methylate; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In propan-1-ol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0039-128X(03)00145-4

Reference yield:

3-benzyloxyestra-1,3,5(10)-trien-17-one (858-98-0) → 3-benzyloxy-estra-1,3,5(10),16-tetraeno[17,16-e]-2'-(N-tert-butoxycarbonyl-glycyl-S-benzyl-L-cysteinylamino)pyrimidine (669056-36-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / sodium methoxide / toluene

2: 77 percent / benzene / Heating

3: 86 percent / NaOMe / propan-1-ol / 70 h / 80 - 90 °C

4: 43 percent / DCC / CH₂Cl₂ / 7 h / 20 °C

5: 95 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

6: 61 percent / DCC / CH₂Cl₂ / 4 h / 20 °C

With sodium methylate; dicyclohexyl-carbodiimide; trifluoroacetic acid; In propan-1-ol; dichloromethane; toluene; benzene;

DOI:10.1016/S0039-128X(03)00145-4

upstream raw materials:

BOC-glycine

3-benzyloxy-estra-1,3,5⁽¹⁰⁾,16-tetraeno[17,16-e]-2'-(S-benzyl-L-cysteinylamino)pyrimidine

Estrone

3-benzyloxyestra-1,3,5⁽¹⁰⁾-trien-17-one

Downstream raw materials:

3-benzyloxy-estra-1,3,5⁽¹⁰⁾,16-tetraeno[17,16-e]-2'-(glycyl-S-benzyl-L-cysteinylamino)pyrimidine

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