R(-)-Dihydro-5-trityloxymethyl-2(3H)-furanone

Base Information

• Chemical Name: R(-)-Dihydro-5-trityloxymethyl-2(3H)-furanone
• CAS No.: 78158-90-4
• Molecular Formula: C24H22 O3
• Molecular Weight: 358.437
• DSSTox Substance ID: DTXSID20511961
• Nikkaji Number: J1.287.685H
• Wikidata: Q82371015
• Mol file: 78158-90-4.mol

Synonyms:78158-90-4;R(-)-Dihydro-5-trityloxymethyl-2(3H)-furanone;(5R)-5-(trityloxymethyl)oxolan-2-one;S(+)-Dihydro-5-trityloxymethyl-2(3H)-furanone;DTXSID20511961;AKOS015893970;(5R)-5-[(Triphenylmethoxy)methyl]oxolan-2-one;(R)-5-(trityloxymethyl)dihydrofuran-2(3H)-one;(R)-(-)- gamma -Trityloxymethyl- gamma -butyrolactone;(R)-(-)-gamma-Trityloxymethyl-gamma-butyrolactone, 98%

Chemical Property of R(-)-Dihydro-5-trityloxymethyl-2(3H)-furanone

Chemical Property:

• Vapor Pressure: 1.33E-10mmHg at 25°C
• Melting Point: 150-152 °C(lit.)
• Refractive Index: 1.591
• Boiling Point: 512.1°C at 760 mmHg
• Flash Point: 222.1°C
• Density: 1.163g/cm³
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 358.15689456
• Heavy Atom Count: 27
• Complexity: 425

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-(?)-γ-Trityloxymethyl-γ-butyrolactone 98% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)OC1COC(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4
• Isomeric SMILES: C1CC(=O)O[C@H]1COC(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4
• Uses: This compound was used in the synthesis of target pentonolactones for interaction studies of γ-lactones with the phorbol ester receptor of protein kinase

Technology Process of R(-)-Dihydro-5-trityloxymethyl-2(3H)-furanone

There total 7 articles about R(-)-Dihydro-5-trityloxymethyl-2(3H)-furanone 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: 95.0%

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) + trityl chloride (76-83-5) → (5R)-5-<(triphenylmethoxy)methyl>-γ-butyrolactone (78158-90-4)

Guidance literature:

In pyridine; at 90 ℃; for 24h;

DOI:10.1080/07328319608007389

Reference yield: 80.0%

(S)-(+)-4-Hydroxy-5-trityloxypentanoic acid (78158-89-1) → (5R)-5-<(triphenylmethoxy)methyl>-γ-butyrolactone (78158-90-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; benzene; for 24h; Ambient temperature;

DOI:10.1055/s-1981-29406

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (5R)-5-<(triphenylmethoxy)methyl>-γ-butyrolactone (78158-90-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / pyridine / 20 h / Ambient temperature

2: 95 percent / KOH / methanol / 1 h / 60 °C

3: 80 percent / triphenylphosphine, diethyl azodicarboxylate / benzene; tetrahydrofuran / 24 h / Ambient temperature

With pyridine; potassium hydroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; benzene;

DOI:10.1055/s-1981-29406

upstream raw materials:

(S)-(+)-4-Hydroxy-5-trityloxypentanoic acid

(5S)-5-[(trityloxy)methyl]tetrahydro-2-furanone

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

trityl chloride

Downstream raw materials:

(5R)-5-<(triphenylmethoxy)methyl>-γ-butyrolactol

2(S)-methyl-(R)-(-)-γ-trityloxymethyl-γ-butyrolactone

2(R)-methyl-(R)-(-)-γ-trityloxymethyl-γ-butyrolactone

amphidinolide C

Refernces

• 1、 Valot, Ga?lle,Regens, Christopher S.,O'Malley, Daniel P.,Godineau, Edouard,Takikawa, Hiroshi,Fürstner, Alois. "Total synthesis of amphidinolide f". supporting information. p. 9534 - 9538. Retrieved 2013/09/23.
• 2、 Deng, Li-Sheng,Huang, Xiao-Ping,Zhao, Gang. "Stereocontrolled and convergent total synthesis of amphidinolide T3". . p. 4625 - 4635. Retrieved 2007/10/03.