(3S)-3-{2-[(Methanesulfonyl)oxy]ethoxy}-4-(triphenylmethoxy)butyl methanesulfonate

Base Information

• Chemical Name: (3S)-3-{2-[(Methanesulfonyl)oxy]ethoxy}-4-(triphenylmethoxy)butyl methanesulfonate
• CAS No.: 170277-77-7
• Molecular Formula: C27H32 O8 S2
• Molecular Weight: 548.678
• DSSTox Substance ID: DTXSID00436749
• Nikkaji Number: J946.172H
• Wikidata: Q76415266
• Mol file: 170277-77-7.mol

Synonyms:170277-77-7;(3S)-3-{2-[(Methanesulfonyl)oxy]ethoxy}-4-(triphenylmethoxy)butyl methanesulfonate;[(3S)-3-(2-methylsulfonyloxyethoxy)-4-trityloxybutyl] methanesulfonate;SCHEMBL3623796;DTXSID00436749;(S)-1-(Mesyloxy)-4-(trityloxy)-3-[2-(mesyloxy)ethoxy]butane;(S)-3-[2-[(methylsulfonyl)oxy]ethoxy]-4-(triphenylmethoxy)-1-butanol methane sulfonate

Chemical Property of (3S)-3-{2-[(Methanesulfonyl)oxy]ethoxy}-4-(triphenylmethoxy)butyl methanesulfonate

Chemical Property:

• Boiling Point: 721.7±60.0 °C(Predicted)
• PSA: 121.96000
• Density: 1.267±0.06 g/cm3(Predicted)
• LogP: 5.88440
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 15
• Exact Mass: 548.15386032
• Heavy Atom Count: 37
• Complexity: 798

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)OCCC(COC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)OCCOS(=O)(=O)C
• Isomeric SMILES: CS(=O)(=O)OCC[C@@H](COC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)OCCOS(=O)(=O)C
• General Description: (3S)-3-[2-(MESYLOXY)ETHOXY]-4-(TRITYLOXY)BUTYL METHANESULFONATE is a key chiral intermediate in the synthesis of the protein kinase C inhibitor LY333531. It can be synthesized via a hetero Diels-Alder and biocatalytic approach, yielding the (S)-enantiomer with high optical purity (>99% ee) and chemical purity. Alternatively, a highly diastereoselective hetero-Diels-Alder reaction using N-glyoxyloyl-(2R)-bornane-10,2-sultam provides an efficient route to this homochiral compound. The intermediate features a mesylate and trityl-protected hydroxyl group, making it useful for further derivatization in pharmaceutical synthesis.

Technology Process of (3S)-3-{2-[(Methanesulfonyl)oxy]ethoxy}-4-(triphenylmethoxy)butyl methanesulfonate

There total 11 articles about (3S)-3-{2-[(Methanesulfonyl)oxy]ethoxy}-4-(triphenylmethoxy)butyl methanesulfonate 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: 88.0%

methanesulfonyl chloride (124-63-0) + (3S)-3-(2-hydroxyethoxy)-4-(triphenylmethoxy)-1-butanol (170277-79-9) → (S)-3-[2-{(methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methanesulfonate (170277-77-7)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 5 ℃; 1-2 h;

DOI:10.1021/jo971980h

Reference yield: 44.0%

(S)-3-(2-benzyloxyethoxy)-4-trityloxybutanol + methanesulfonyl chloride (124-63-0) → (S)-3-[2-{(methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methanesulfonate (170277-77-7)

Guidance literature:

With triethylamine; In toluene;

Reference yield:

trityl chloride (76-83-5) → (S)-3-[2-{(methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methanesulfonate (170277-77-7)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / CH₂Cl₂ / 24 h / 20 - 25 °C

2: 1.) CuI / 1.) THF, -30 deg C, 15 min, 2.) THF, -30 deg C, 1 h

3: 1.) potassium tert-butoxide / 1.) THF, 45 deg C, 45 min; other reagents: NaH, NaOH/tetrabutylammonium bromide, NaOH/tetrabutylammonium fluoride, 2.) THF, 21 deg C, 1 h

4: 1.) ozone, Sudan red, 2.) NaBH₄, NaOH / 1.) CH₂Cl₂, ethanol, 2.) CH₂Cl₂, ethanol, 25 deg C, 12-16 h

5: 88 percent / triethylamine / CH₂Cl₂ / 0 - 5 °C / 1-2 h

With sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; sudan red; potassium tert-butylate; ozone; triethylamine; In dichloromethane;

DOI:10.1021/jo971980h

upstream raw materials:

methanesulfonyl chloride

(3S)-3-(2-hydroxyethoxy)-4-(triphenylmethoxy)-1-butanol

trityl chloride

(S)-tritylglycidol

Downstream raw materials:

(9S)-6,7,10,11-tetrahydro-19-methyl-9-[(triphenylmethoxy)-methyl]-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h]-[1,4,13]oxadiazacyclohexadecine-18,20(19H)-dione

(S)-4-(triphenylmethoxy)-2-(2-chloroethoxy)-1-chlorobutane

(S)-4-(triphenylmethoxy)-2-(2-iodoethoxy)-1-iodobutane