N,N-DIBENZYL-O-(T-BUTYLDIMETHYLSILYL)-L-SERINE METHYL ESTER

Base Information

• Chemical Name: N,N-DIBENZYL-O-(T-BUTYLDIMETHYLSILYL)-L-SERINE METHYL ESTER
• CAS No.: 352530-50-8
• Molecular Formula: C24H35NO3Si
• Molecular Weight: 413.632
• European Community (EC) Number: 688-215-1
• DSSTox Substance ID: DTXSID10463208
• Nikkaji Number: J1.715.987I
• Wikidata: Q76416987
• Mol file: 352530-50-8.mol

Synonyms:352530-50-8;N,N-Dibenzyl-O-(t-butyldimethylsilyl)-L-serine methyl ester;methyl (2S)-3-[tert-butyl(dimethyl)silyl]oxy-2-(dibenzylamino)propanoate;DTXSID10463208;Methyl N,N-dibenzyl-O-(tert-butyldimethylsilyl)-L-serinate;Methyl N,N-dibenzyl-O-[tert-butyl(dimethyl)silyl]-L-serinate

Chemical Property of N,N-DIBENZYL-O-(T-BUTYLDIMETHYLSILYL)-L-SERINE METHYL ESTER

Chemical Property:

• Vapor Pressure: 5.33E-08mmHg at 25°C
• Refractive Index: n20/D 1.5160(lit.)
• Boiling Point: 441.7oC at 760 mmHg
• Flash Point: 100oC
• PSA: 38.77000
• Density: 1.046 g/mL at 25oC(lit.)
• LogP: 5.25220
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 413.23862051
• Heavy Atom Count: 29
• Complexity: 471

Purity/Quality:

98%Min ^*data from raw suppliers

N,N-DIBENZYL-O-(T-BUTYLDIMETHYLSILYL)-L-SERINE METHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCC(C(=O)OC)N(CC1=CC=CC=C1)CC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)[Si](C)(C)OC[C@@H](C(=O)OC)N(CC1=CC=CC=C1)CC2=CC=CC=C2

Technology Process of N,N-DIBENZYL-O-(T-BUTYLDIMETHYLSILYL)-L-SERINE METHYL ESTER

There total 2 articles about N,N-DIBENZYL-O-(T-BUTYLDIMETHYLSILYL)-L-SERINE METHYL 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: 97.0%

tert-butyldimethylsilyl chloride (18162-48-6) + methyl (2S)-2-(dibenzylamino)-3-hydroxypropanoate (88099-67-6) → methyl (S)-3-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)propanoate (352530-50-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane;

DOI:10.3390/molecules15031291

Reference yield:

benzyl bromide (100-39-0) → methyl (S)-3-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)propanoate (352530-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / tetrahydrofuran; dimethyl sulfoxide / Reflux

2: 1H-imidazole / dichloromethane / 12 h / 50 °C

With 1H-imidazole; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jacs.1c09616

Reference yield: 90.0%

Chloroiodomethane (593-71-5) + methyl (S)-3-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)propanoate (352530-50-8) → (-)-(3S)-3-(dibenzylamino)-4-[(tert-butyldimethylsilanyl)oxy]-1-chlorobutan-2-one (388632-20-0)

Guidance literature:

With methyllithium; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.5h;

DOI:10.1021/jo015920u

upstream raw materials:

tert-butyldimethylsilyl chloride

methyl (2S)-2-(dibenzylamino)-3-hydroxypropanoate

benzyl bromide

Downstream raw materials:

(-)-(3S)-3-(dibenzylamino)-4-[(tert-butyldimethylsilanyl)oxy]-1-chlorobutan-2-one

methyl (S)-2-benzylamino-3-(tert-butyldimethylsilyloxy)propionate

(3S,5R,6R)-3-[(1S,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-1-hydroxy-propyl]-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxan-2-one

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-propionaldehyde