(3R,2'R)-6-(benzyloxy)-1-((tert-butyloxy)carbonyl)-3-(hydroxymethyl)indoline R-(-)-O-acetylmandelic ester

Base Information

• Chemical Name: (3R,2'R)-6-(benzyloxy)-1-((tert-butyloxy)carbonyl)-3-(hydroxymethyl)indoline R-(-)-O-acetylmandelic ester
• CAS No.: 127943-71-9
• Molecular Formula: C₃₁H₃₃NO₇
• Molecular Weight: 531.606
• Mol file: 127943-71-9.mol

Synonyms:(3R,2'R)-6-(benzyloxy)-1-((tert-butyloxy)carbonyl)-3-(hydroxymethyl)indoline R-(-)-O-acetylmandelic ester

Chemical Property of (3R,2'R)-6-(benzyloxy)-1-((tert-butyloxy)carbonyl)-3-(hydroxymethyl)indoline R-(-)-O-acetylmandelic ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,2'R)-6-(benzyloxy)-1-((tert-butyloxy)carbonyl)-3-(hydroxymethyl)indoline R-(-)-O-acetylmandelic ester

There total 7 articles about (3R,2'R)-6-(benzyloxy)-1-((tert-butyloxy)carbonyl)-3-(hydroxymethyl)indoline R-(-)-O-acetylmandelic 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:

(R)-(-)-O-acetylmandelic acid (51019-43-3) + 6-benzyloxy-1-tert-butyloxycarbonyl-2,3-dihydro-1H-indole-3-methanol (151384-87-1) → (3S,2'R)-6-(benzyloxy)-1-((tert-butyloxy)carbonyl)-3-(hydroxymethyl)indoline R-(-)-O-acetylmandelic ester (127943-72-0) + (3R,2'R)-6-(benzyloxy)-1-((tert-butyloxy)carbonyl)-3-(hydroxymethyl)indoline R-(-)-O-acetylmandelic ester (127943-71-9)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 23 ℃; for 9h; Yield given. Yields of byproduct given;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (3R,2'R)-6-(benzyloxy)-1-((tert-butyloxy)carbonyl)-3-(hydroxymethyl)indoline R-(-)-O-acetylmandelic ester (127943-71-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / dioxane / 10 h / 105 °C

2: 1.) sodium hydride / 1.) THF, DMF, 2.) RT, 3 h

3: 91 percent / tri-n-butyltin hydride, 2,2'-azobis(2-methylpropionitrile (AIBN) / benzene / 3 h / Heating

4: 1.) O₃, 2.) sodium borohydride / 1.) ethanol, dichloromethane, -78 deg C, 3 min, 2.) water, RT, 4 h

5: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (EDCI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 9 h / 23 °C

With dmap; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; dichloromethane; benzene;

Reference yield:

3-(benzyloxy)aniline (1484-26-0) → (3R,2'R)-6-(benzyloxy)-1-((tert-butyloxy)carbonyl)-3-(hydroxymethyl)indoline R-(-)-O-acetylmandelic ester (127943-71-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 60 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -78 °C

2: 85 percent / dioxane / 10 h / 105 °C

3: 1.) sodium hydride / 1.) THF, DMF, 2.) RT, 3 h

4: 91 percent / tri-n-butyltin hydride, 2,2'-azobis(2-methylpropionitrile (AIBN) / benzene / 3 h / Heating

5: 1.) O₃, 2.) sodium borohydride / 1.) ethanol, dichloromethane, -78 deg C, 3 min, 2.) water, RT, 4 h

6: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (EDCI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 9 h / 23 °C

With dmap; sodium tetrahydroborate; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; sodium hydride; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; benzene;

upstream raw materials:

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

6-benzyloxy-1-tert-butyloxycarbonyl-2,3-dihydro-1H-indole-3-methanol

di-tert-butyl dicarbonate

3-(benzyloxy)aniline

Refernces