1-[N-BENZYLOXYCARBONYL-(1S,2R)-1-AMINO-2-HYDROXYPROPYL]-4-METHYL-2,6,7-TRIOXABICYCLO[2.2.2]OCTANE

Base Information

• Chemical Name: 1-[N-BENZYLOXYCARBONYL-(1S,2R)-1-AMINO-2-HYDROXYPROPYL]-4-METHYL-2,6,7-TRIOXABICYCLO[2.2.2]OCTANE
• CAS No.: 206191-48-2
• Molecular Formula: C17H23 N O6
• Molecular Weight: 337.373
• Mol file: 206191-48-2.mol

Synonyms:Carbamicacid, [(1S,2R)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)propyl]-,phenylmethyl ester (9CI); Carbamic acid,[2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)propyl]-,phenylmethyl ester, [R-(R*,S*)]-

Chemical Property of 1-[N-BENZYLOXYCARBONYL-(1S,2R)-1-AMINO-2-HYDROXYPROPYL]-4-METHYL-2,6,7-TRIOXABICYCLO[2.2.2]OCTANE

Chemical Property:

• PSA: 86.25000
• LogP: 1.79020

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-[N-BENZYLOXYCARBONYL-(1S,2R)-1-AMINO-2-HYDROXYPROPYL]-4-METHYL-2,6,7-TRIOXABICYCLO[2.2.2]OCTANE

There total 7 articles about 1-[N-BENZYLOXYCARBONYL-(1S,2R)-1-AMINO-2-HYDROXYPROPYL]-4-METHYL-2,6,7-TRIOXABICYCLO[2.2.2]OCTANE 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: 50.0%

methylmagnesium bromide (75-16-1) + 1-[N-(benzyloxycarbonyl)-(1S)-1-amino-2-oxoethyl]-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane (183671-34-3) → benzyl ((1S,2R)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propyl)carbamate (206191-48-2)

Guidance literature:

methylmagnesium bromide; 1-[N-(benzyloxycarbonyl)-(1S)-1-amino-2-oxoethyl]-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane; In diethyl ether; dichloromethane; at -78 ℃; for 0.025h; Inert atmosphere; Cooling with ice;

With ammonium chloride; In diethyl ether; dichloromethane; for 0.25h;

Reference yield:

(3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate (99314-44-0) → benzyl ((1S,2R)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propyl)carbamate (206191-48-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / NaBr / acetone / 30 h / Heating

2: 1.) Cs₂CO₃ / 1.) H₂O, 20 min, 2.) DMF, room temperature, 24 h

3: 1.) BF₃*Et₂O, 2.) TEA / 1.) CH₂Cl₂, 0 deg C to room temperature, 6 h, 2.) 30 min

With TEA; boron trifluoride diethyl etherate; caesium carbonate; sodium bromide; In acetone;

DOI:10.1021/jo972294l

Reference yield:

3-hydroxymethyl-3-methyloxethane (3143-02-0) → benzyl ((1S,2R)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propyl)carbamate (206191-48-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / pyridine / 1.5 h

2: 92 percent / NaBr / acetone / 30 h / Heating

3: 1.) Cs₂CO₃ / 1.) H₂O, 20 min, 2.) DMF, room temperature, 24 h

4: 1.) BF₃*Et₂O, 2.) TEA / 1.) CH₂Cl₂, 0 deg C to room temperature, 6 h, 2.) 30 min

With TEA; boron trifluoride diethyl etherate; caesium carbonate; sodium bromide; In pyridine; acetone;

DOI:10.1021/jo972294l

upstream raw materials:

(2S,3R)-2-Benzyloxycarbonylamino-3-hydroxy-butyric acid 3-methyl-oxetan-3-ylmethyl ester

3-hydroxymethyl-3-methyloxethane

N-benzyloxycarbonyl-L-treonine

(3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate

Downstream raw materials:

1-[(N-benzyloxycarbonyl)-(1S)-1-amino-(2S)-2-azidopropyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

benzyl ((1S,2R)-2-(4-(benzyloxy)phenyl)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propyl)carbamate

4-((1S,2R)-1-amino-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propan-2-yl)phenol

4-((4-aminophenyl)buta-1,3-diyn-1-yl)-N-((1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propyl)benzamide