[(4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: [(4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate
• CAS No.: 73987-14-1
• Molecular Formula: C₁₄H₂₀O₅S
• Molecular Weight: 300.376
• NSC Number: 75723
• DSSTox Substance ID: DTXSID50995255
• Wikidata: Q82986568
• Mol file: 73987-14-1.mol

Synonyms:73987-14-1;NSC75723;DTXSID50995255;NSC-75723;WLN: T5O COTJ B1 B1 D1OSWR D1& E1 -DL;1, 2,2,4-trimethyl-, p-toluenesulfonate (ester), dl-erythro-;1, 2,2,5-trimethyl-, 4-methylbenzenesulfonate, cis-(.+-.)-;(2,2,5-Trimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzene-1-sulfonate;2,4-Trimethyl-5-(p-tolylsulfonyloxy)methyl-dl-erythro-1,3-dioxolane

Chemical Property of [(4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate

Chemical Property:

• Vapor Pressure: 2.04E-06mmHg at 25°C
• Boiling Point: 405.6°C at 760 mmHg
• Flash Point: 199.1°C
• Density: 1.159g/cm³
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 300.10314491
• Heavy Atom Count: 20
• Complexity: 417

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(OC(O1)(C)C)COS(=O)(=O)C2=CC=C(C=C2)C
• Isomeric SMILES: C[C@H]1[C@H](OC(O1)(C)C)COS(=O)(=O)C2=CC=C(C=C2)C

Technology Process of [(4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate

There total 13 articles about [(4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate 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: 85.0%

(4S,5S)-4-hydroxymethyl-2,2,5-trimethyl-[1,3]-dioxolane (41167-51-5,57626-73-0,67195-07-7,73679-52-4,73679-54-6,81739-14-2,111319-77-8,85249-45-2) + p-toluenesulfonyl chloride (98-59-9) → (-)-1-O-p-toluenesulfonyl-4-deoxy-2,3-O-isopropylidene-L-threytol (73987-14-1,81739-15-3,85249-46-3,92344-88-2)

Guidance literature:

With pyridine; at 0 ℃; for 2.5h;

DOI:10.1016/S0040-4020(01)86801-0

Reference yield: 40.0%

(RS)-2,2,4-trimethyl-1,3-dioxolan-5-ylmethanol (81739-14-2) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-ylmethyl ester (73987-14-1,81739-15-3,85249-46-3,92344-88-2)

Guidance literature:

With pyridine; at 0 ℃; for 3h;

Reference yield:

[(4S,5S)-2,2-Dimethyl-5-(toluene-4-sulfonylmethoxymethyl)-[1,3]dioxolan-4-yl]-methanol → (-)-1-O-p-toluenesulfonyl-4-deoxy-2,3-O-isopropylidene-L-threytol (73987-14-1,81739-15-3,85249-46-3,92344-88-2)

Guidance literature:

Multi-step reaction with 3 steps

1: NaI / acetone / 100 °C

2: Pd/C / ethanol

With sodium iodide; palladium on activated charcoal; In ethanol; acetone;

DOI:10.1016/S0040-4039(01)91182-7

upstream raw materials:

(RS)-2,2,4-trimethyl-1,3-dioxolan-5-ylmethanol

p-toluenesulfonyl chloride

(4S,5R)-2,2,5-Trimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

erythro-2,3-O-isopropylidenedioxybutan-1-ol

Downstream raw materials:

[4-(3-Chloro-benzyloxy)-phenyl]-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-ylmethyl)-amine

(-)-1-O-p-toluenesulfonyl-4-deoxy-L-threytol