tert-butyl (R)-2-acetoxy-5-(1-benzyloxycarbonyl-2-tert-butoxycarbonylhydrazino)pentanoate

Base Information

Chemical Name:tert-butyl (R)-2-acetoxy-5-(1-benzyloxycarbonyl-2-tert-butoxycarbonylhydrazino)pentanoate
CAS No.:176237-53-9
Molecular Formula:C₂₄H₃₆N₂O₈
Molecular Weight:480.558
Hs Code.:

Synonyms:tert-butyl (R)-2-acetoxy-5-(1-benzyloxycarbonyl-2-tert-butoxycarbonylhydrazino)pentanoate

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Chemical Property of tert-butyl (R)-2-acetoxy-5-(1-benzyloxycarbonyl-2-tert-butoxycarbonylhydrazino)pentanoate

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Technology Process of tert-butyl (R)-2-acetoxy-5-(1-benzyloxycarbonyl-2-tert-butoxycarbonylhydrazino)pentanoate

There total 9 articles about tert-butyl (R)-2-acetoxy-5-(1-benzyloxycarbonyl-2-tert-butoxycarbonylhydrazino)pentanoate 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: 94.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 176237-52-8
tert-butyl (R)-2-acetoxy-5-(2-tert-butoxycarbonylhydrazino)pentanoate

: 176237-53-9
tert-butyl (R)-2-acetoxy-5-(1-benzyloxycarbonyl-2-tert-butoxycarbonylhydrazino)pentanoate

Guidance literature:: With sodium hydrogencarbonate; In 1,4-dioxane; for 12h; Ambient temperature;
DOI:10.1055/s-1996-4192

Reference yield:

: 53558-94-4
(R)-(-)-γ-chlorocarbonyl-γ-butyrolactone

: 176237-53-9
tert-butyl (R)-2-acetoxy-5-(1-benzyloxycarbonyl-2-tert-butoxycarbonylhydrazino)pentanoate

Guidance literature:: Multi-step reaction with 9 steps

1: 91 percent / pyridine / CH₂Cl₂ / -30 - 20 °C

2: 92 percent / DIBAL / hexane; tetrahydrofuran / 1 h / -40 °C

3: 95 percent / DMAP, NEt₃ / CH₂Cl₂ / 3 h

4: 93 percent / DMAP, pyridine / CH₂Cl₂ / 16 h / Ambient temperature

5: 88 percent / 40percent aq. HF / acetonitrile / 0.5 h / Ambient temperature

6: 83 percent / (COCl)2, DMSO / CH₂Cl₂ / 0.25 h / -60 - -50 °C

7: 97 percent / HOAc / toluene / 0.08 h / Ambient temperature

8: 100 percent / H₂, HOAc / PtO₂ / ethanol / 24 h / 2250.2 Torr / Ambient temperature

9: 94 percent / aq. NaHCO₃ / dioxane / 12 h / Ambient temperature

With pyridine; dmap; oxalyl dichloride; hydrogen fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; triethylamine; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; toluene; acetonitrile;
DOI:10.1055/s-1996-4192

Reference yield:

: 176237-48-2
2-(R)-5-oxotetrahydrofuran-2-carboxylic acid, tert-butyl ester

: 176237-53-9
tert-butyl (R)-2-acetoxy-5-(1-benzyloxycarbonyl-2-tert-butoxycarbonylhydrazino)pentanoate

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / DIBAL / hexane; tetrahydrofuran / 1 h / -40 °C

2: 95 percent / DMAP, NEt₃ / CH₂Cl₂ / 3 h

3: 93 percent / DMAP, pyridine / CH₂Cl₂ / 16 h / Ambient temperature

4: 88 percent / 40percent aq. HF / acetonitrile / 0.5 h / Ambient temperature

5: 83 percent / (COCl)2, DMSO / CH₂Cl₂ / 0.25 h / -60 - -50 °C

6: 97 percent / HOAc / toluene / 0.08 h / Ambient temperature

7: 100 percent / H₂, HOAc / PtO₂ / ethanol / 24 h / 2250.2 Torr / Ambient temperature

8: 94 percent / aq. NaHCO₃ / dioxane / 12 h / Ambient temperature

With pyridine; dmap; oxalyl dichloride; hydrogen fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; triethylamine; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; toluene; acetonitrile;
DOI:10.1055/s-1996-4192