methyl (+)-(3R,5R)-5-{[(tert-butyl)diphenylsilyl]oxy}-3-(tosylamino)decanoate

Base Information

• Chemical Name: methyl (+)-(3R,5R)-5-{[(tert-butyl)diphenylsilyl]oxy}-3-(tosylamino)decanoate
• CAS No.: 524011-03-8
• Molecular Formula: C₃₄H₄₇NO₅SSi
• Molecular Weight: 609.902
• Mol file: 524011-03-8.mol

Synonyms:methyl (+)-(3R,5R)-5-{[(tert-butyl)diphenylsilyl]oxy}-3-(tosylamino)decanoate

Chemical Property of methyl (+)-(3R,5R)-5-{[(tert-butyl)diphenylsilyl]oxy}-3-(tosylamino)decanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (+)-(3R,5R)-5-{[(tert-butyl)diphenylsilyl]oxy}-3-(tosylamino)decanoate

There total 6 articles about methyl (+)-(3R,5R)-5-{[(tert-butyl)diphenylsilyl]oxy}-3-(tosylamino)decanoate 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: 54.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + p-toluenesulfonyl chloride (98-59-9) + tert-butylchlorodiphenylsilane (58479-61-1) + ethyl (-)-(4R,6R)-3,4,5,6-tetrahydro-2-oxo-6-pentyl-2H-1,3-oxazine-4-acetate (524011-08-3) → methyl (+)-(3R,5R)-5-{[(tert-butyl)diphenylsilyl]oxy}-3-(tosylamino)decanoate (524011-03-8)

Guidance literature:

Multistep reaction;

DOI:10.1002/hlca.200390016

Reference yield:

(3R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octanal (111633-54-6) → methyl (+)-(3R,5R)-5-{[(tert-butyl)diphenylsilyl]oxy}-3-(tosylamino)decanoate (524011-03-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 1 h / 20 °C

2.1: 637 mg / p-toluenesulfonic acid monohydrate / methanol / 1 h / 20 °C

3.1: CH₂Cl₂ / 1 h / -78 - -60 °C

3.2: 94 percent / H₂O / CH₂Cl₂ / 4 h / 60 °C

4.1: 80 percent / potassium tert-butoxide / tetrahydrofuran / 2.5 h / 0 °C

With potassium tert-butylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1.1: Horner-Wadsworth-Emmons reaction / 4.1: aza-Michael cyclization;

DOI:10.1002/hlca.200390016

Reference yield:

(3R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octanol → methyl (+)-(3R,5R)-5-{[(tert-butyl)diphenylsilyl]oxy}-3-(tosylamino)decanoate (524011-03-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1.10 g / PDC / CH₂Cl₂ / 4 h / Heating

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 1 h / 20 °C

3.1: 637 mg / p-toluenesulfonic acid monohydrate / methanol / 1 h / 20 °C

4.1: CH₂Cl₂ / 1 h / -78 - -60 °C

4.2: 94 percent / H₂O / CH₂Cl₂ / 4 h / 60 °C

5.1: 80 percent / potassium tert-butoxide / tetrahydrofuran / 2.5 h / 0 °C

With dipyridinium dichromate; potassium tert-butylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 2.1: Horner-Wadsworth-Emmons reaction / 5.1: aza-Michael cyclization;

DOI:10.1002/hlca.200390016

upstream raw materials:

diazomethane

p-toluenesulfonyl chloride

tert-butylchlorodiphenylsilane

ethyl (-)-(4R,6R)-3,4,5,6-tetrahydro-2-oxo-6-pentyl-2H-1,3-oxazine-4-acetate

Downstream raw materials:

methyl (-)-(3R,5R)-3-{[(3-aminopropyl)tosyl]amino}-5-{[(tert-butyl)diphenylsilyl]oxy}decanoate

(-)-(4R)-4-{(2R)-2-{[(tert-butyl)diphenylsilyl]oxy}heptyl}hexahydro-5-tosyl-1,5-diazocin(1H)-2-one

methyl (3R,5R)-3-{{{3-[(tert-butoxy)carbonyl]amino}propyl}tosyl}amino-5-{[(tert-butyl)diphenylsilyl]oxy}decanoate