1,1-DIMETHYLETHYL (1S,2R)-2-HYDROXY-1-(4-METHYL-2,6,7-TRIOXABICYCLO[2.2.2]OCTANYL)PROPYLCARBAMATE

Base Information

• Chemical Name: 1,1-DIMETHYLETHYL (1S,2R)-2-HYDROXY-1-(4-METHYL-2,6,7-TRIOXABICYCLO[2.2.2]OCTANYL)PROPYLCARBAMATE
• CAS No.: 206191-49-3
• Molecular Formula: C₁₄H₂₅NO₆
• Molecular Weight: 303.356
• Mol file: 206191-49-3.mol

Synonyms:Carbamicacid, [2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)propyl]-,1,1-dimethylethyl ester, [R-(R*,S*)]-

Chemical Property of 1,1-DIMETHYLETHYL (1S,2R)-2-HYDROXY-1-(4-METHYL-2,6,7-TRIOXABICYCLO[2.2.2]OCTANYL)PROPYLCARBAMATE

Chemical Property:

• PSA: 86.25000
• LogP: 1.38850

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,1-DIMETHYLETHYL (1S,2R)-2-HYDROXY-1-(4-METHYL-2,6,7-TRIOXABICYCLO[2.2.2]OCTANYL)PROPYLCARBAMATE

There total 11 articles about 1,1-DIMETHYLETHYL (1S,2R)-2-HYDROXY-1-(4-METHYL-2,6,7-TRIOXABICYCLO[2.2.2]OCTANYL)PROPYLCARBAMATE 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:

(3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate (99314-44-0) → 1-(N-tert-butyloxycarbonyl-(1S,2R)-1-amino-2-hydroxypropyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (206191-49-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Cs₂CO₃, 2.) NaI / 1.) H₂O, 2.) DMF, room temperature, 48 h

2: 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 iodide;

DOI:10.1021/jo972294l

Reference yield:

(3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate (99314-44-0) → 1-(N-tert-butyloxycarbonyl-(1S,2S)-1-amino-2-hydroxypropyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (206191-49-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) Cs₂CO₃, 2.) NaI / 1.) H₂O, 2.) DMF, room temperature, 48 h

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

3: 1.) DMSO, (COCl)2, 2.) DIPEA / 1.) CH₂Cl₂, -78 deg C, 1.5 h, 2.) -78 deg C, 30 min; 0 deg C, 10 min

4: diethyl ether; toluene / 0.08 h / -78 °C

With oxalyl dichloride; TEA; boron trifluoride diethyl etherate; caesium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; sodium iodide; In diethyl ether; toluene;

DOI:10.1021/jo972294l

Reference yield:

3-hydroxymethyl-3-methyloxethane (3143-02-0) → 1-(N-tert-butyloxycarbonyl-(1S,2R)-1-amino-2-hydroxypropyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (206191-49-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / pyridine / 1.5 h

2: 1.) Cs₂CO₃, 2.) NaI / 1.) H₂O, 2.) DMF, room temperature, 48 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 iodide; In pyridine;

DOI:10.1021/jo972294l

upstream raw materials:

methylmagnesium bromide

1-(N-tert-butyloxycarbonyl-(1S)-1-amino-2-oxoethyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

3-hydroxymethyl-3-methyloxethane

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