(1R,2'R,2''R)-methyl 3-((tert-butyloxy)carbonyl)-5-hydroxy-1-(hydroxymethyl)-1,2-dihydro-3H-pyrrolo<3,2-e>indole-7-carboxylate, bis((R)-O-acetylmandelate ester)

Base Information

• Chemical Name: (1R,2'R,2''R)-methyl 3-((tert-butyloxy)carbonyl)-5-hydroxy-1-(hydroxymethyl)-1,2-dihydro-3H-pyrrolo<3,2-e>indole-7-carboxylate, bis((R)-O-acetylmandelate ester)
• CAS No.: 144667-39-0
• Molecular Formula: C₃₈H₃₈N₂O₁₂
• Molecular Weight: 714.726

Synonyms:

Chemical Property of (1R,2'R,2''R)-methyl 3-((tert-butyloxy)carbonyl)-5-hydroxy-1-(hydroxymethyl)-1,2-dihydro-3H-pyrrolo<3,2-e>indole-7-carboxylate, bis((R)-O-acetylmandelate ester)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2'R,2''R)-methyl 3-((tert-butyloxy)carbonyl)-5-hydroxy-1-(hydroxymethyl)-1,2-dihydro-3H-pyrrolo<3,2-e>indole-7-carboxylate, bis((R)-O-acetylmandelate ester)

There total 34 articles about (1R,2'R,2''R)-methyl 3-((tert-butyloxy)carbonyl)-5-hydroxy-1-(hydroxymethyl)-1,2-dihydro-3H-pyrrolo<3,2-e>indole-7-carboxylate, bis((R)-O-acetylmandelate 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:

O-Benzyl-N2,N5-dibenzoyl-2,5-diamino-4-(1,1-bis(methoxycarbonyl)methyl)phenol (124400-60-8) → (1S,2'R,2''R)-methyl 3-((tert-butyloxy)carbonyl)-5-hydroxy-1-(hydroxymethyl)-1,2-dihydro-3H-pyrrolo<3,2-e>indole-7-carboxylate, bis((R)-O-acetylmandelate ester) (144667-39-0,144732-56-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 71 percent / NaBH₄ / ethanol / a) 0 deg C, 30 min, b) 25 deg C, 2.5 h

2: 100 percent / TsOH / dimethylformamide / 24 h / 25 °C

3: 100 percent / Pb(OAc)4 / CHCl₃ / 1.5 h / 25 °C

4: 2.) H₂O, phosphate buffer pH 4.0 / 1.) THF, 25 deg C, 10 min, 2.) THF, 25 deg C, 24 h

5: 81 percent / 2 N HCl-CH₃OH / 2 h / 25 °C

6: 100 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 2 h / 25 °C

7: 98percent NH₂NH₂-H₂O / ethanol / 34 h / 145 °C / Heating

8: tetrahydrofuran / 0.33 h / 25 °C

9: 96 percent / phosphate buffer solution pH 4 / dioxane; dimethylsulfoxide / 15 h / 110 °C

10: 92 percent / MnO₂ / CH₂Cl₂; methanol / 12 h / 25 °C

11: 92 percent / 25percent aq. HCO₂NH₄ / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C

12: 137 mg / EDCI, DMAP / CH₂Cl₂ / 2.5 h / 0 °C

With lead(IV) acetate; hydrogenchloride; dmap; manganese(IV) oxide; sodium tetrahydroborate; phosphate buffer pH 4.0; phosphate buffer solution pH 4; water; ammonium formate; toluene-4-sulfonic acid; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/ja00073a019

Reference yield:

O-Benzyl-N2,N5-dibenzoyl-2,5-diamino-4-(1,1-bis(methoxycarbonyl)methyl)phenol (124400-60-8) → (1R,2'R,2''R)-methyl 3-((tert-butyloxy)carbonyl)-5-hydroxy-1-(hydroxymethyl)-1,2-dihydro-3H-pyrrolo<3,2-e>indole-7-carboxylate, bis((R)-O-acetylmandelate ester) (144667-39-0,144732-56-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 71 percent / NaBH₄ / ethanol / a) 0 deg C, 30 min, b) 25 deg C, 2.5 h

2: 100 percent / TsOH / dimethylformamide / 24 h / 25 °C

3: 100 percent / Pb(OAc)4 / CHCl₃ / 1.5 h / 25 °C

4: 2.) H₂O, phosphate buffer pH 4.0 / 1.) THF, 25 deg C, 10 min, 2.) THF, 25 deg C, 24 h

5: 81 percent / 2 N HCl-CH₃OH / 2 h / 25 °C

6: 100 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 2 h / 25 °C

7: 98percent NH₂NH₂-H₂O / ethanol / 34 h / 145 °C / Heating

8: tetrahydrofuran / 0.33 h / 25 °C

9: 96 percent / phosphate buffer solution pH 4 / dioxane; dimethylsulfoxide / 15 h / 110 °C

10: 92 percent / MnO₂ / CH₂Cl₂; methanol / 12 h / 25 °C

11: 92 percent / 25percent aq. HCO₂NH₄ / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C

12: 133 mg / EDCI, DMAP / CH₂Cl₂ / 2.5 h / 0 °C

With lead(IV) acetate; hydrogenchloride; dmap; manganese(IV) oxide; sodium tetrahydroborate; phosphate buffer pH 4.0; phosphate buffer solution pH 4; water; ammonium formate; toluene-4-sulfonic acid; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/ja00073a019

Reference yield:

O-benzyl-N2,N5-dibenzoyl-2,5-diamino-4-(bis(hydroxymethyl)methyl)phenol (144667-27-6) → (1S,2'R,2''R)-methyl 3-((tert-butyloxy)carbonyl)-5-hydroxy-1-(hydroxymethyl)-1,2-dihydro-3H-pyrrolo<3,2-e>indole-7-carboxylate, bis((R)-O-acetylmandelate ester) (144667-39-0,144732-56-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / TsOH / dimethylformamide / 24 h / 25 °C

2: 100 percent / Pb(OAc)4 / CHCl₃ / 1.5 h / 25 °C

3: 2.) H₂O, phosphate buffer pH 4.0 / 1.) THF, 25 deg C, 10 min, 2.) THF, 25 deg C, 24 h

4: 81 percent / 2 N HCl-CH₃OH / 2 h / 25 °C

5: 100 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 2 h / 25 °C

6: 98percent NH₂NH₂-H₂O / ethanol / 34 h / 145 °C / Heating

7: tetrahydrofuran / 0.33 h / 25 °C

8: 96 percent / phosphate buffer solution pH 4 / dioxane; dimethylsulfoxide / 15 h / 110 °C

9: 92 percent / MnO₂ / CH₂Cl₂; methanol / 12 h / 25 °C

10: 92 percent / 25percent aq. HCO₂NH₄ / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C

11: 137 mg / EDCI, DMAP / CH₂Cl₂ / 2.5 h / 0 °C

With lead(IV) acetate; hydrogenchloride; dmap; manganese(IV) oxide; phosphate buffer pH 4.0; phosphate buffer solution pH 4; water; ammonium formate; toluene-4-sulfonic acid; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/ja00073a019

upstream raw materials:

(R)-(-)-O-acetylmandelic acid

methyl 3-((tert-butyloxy)carbonyl)-5-hydroxy-1-(hydroxymethyl)-1,2-dihydro-3H-pyrrolo<3,2-e>indole-7-carboxylate

di-tert-butyl dicarbonate

O-Benzyl-N²,N⁵-dibenzoyl-2,5-diamino-4-(1,1-bis(methoxycarbonyl)methyl)phenol

Downstream raw materials:

duocarmycin

(+)-duocarmycin SA

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