5-O-(Triphenylmethyl)-2-C-methyl-D-ribonic-gamma-lactone

Base Information

• Chemical Name: 5-O-(Triphenylmethyl)-2-C-methyl-D-ribonic-gamma-lactone
• CAS No.: 157666-05-2
• Molecular Formula: C25H24 O5
• Molecular Weight: 404.46
• Mol file: 157666-05-2.mol

Synonyms:5-O-(Triphenylmethyl)-2-C-methyl-D-ribonic-gamma-lactone;5-O-(Triphenylmethyl)-2-C-methyl-D-ribonic-γ-lactone

Chemical Property of 5-O-(Triphenylmethyl)-2-C-methyl-D-ribonic-gamma-lactone

Chemical Property:

• Boiling Point: 545.9±19.0 °C(Predicted)
• PKA: 12.07±0.60(Predicted)
• PSA: 75.99000
• Density: 1.262
• LogP: 3.03240

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-O-(Triphenylmethyl)-2-C-methyl-D-ribonic-gamma-lactone

There total 5 articles about 5-O-(Triphenylmethyl)-2-C-methyl-D-ribonic-gamma-lactone 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: 82.0%

(4S)-4-Triphenylmethyloxymethyl-2-methyl-butenolide (157666-04-1) → 5-O-Triphenylmethyl-2-C-methyl-D-ribono-1,4-lactone (157666-05-2)

Guidance literature:

With potassium permanganate; crown ether; In dichloromethane; at -15 ℃; for 2h;

Reference yield:

2-C-methyl-D-ribono-1,4-lactone (492-30-8,7306-56-1,19774-08-4,36791-96-5,36791-97-6,53008-90-5,53008-96-1,53008-97-2,86204-17-3,86204-18-4,93636-22-7) + trityl chloride (76-83-5) → 5-O-Triphenylmethyl-2-C-methyl-D-ribono-1,4-lactone (157666-05-2)

Guidance literature:

With pyridine; Cooling with ice;

DOI:10.1016/j.tetlet.2018.03.007

Reference yield:

(S)-5-(hydroxymethyl)-3-methylfuran-2(5H)-one (53008-99-4) → 5-O-Triphenylmethyl-2-C-methyl-D-ribono-1,4-lactone (157666-05-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / pyridine / H₂O / 24 h / Ambient temperature

2: 82 percent / KMnO₄, crown ether / CH₂Cl₂ / 2 h / -15 °C

With pyridine; potassium permanganate; crown ether; In dichloromethane; water;

upstream raw materials:

(4S)-4-Triphenylmethyloxymethyl-2-methyl-butenolide

(S)-5-(hydroxymethyl)-3-methylfuran-2(5H)-one

trityl chloride

(2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methyl-2-propenoate

Downstream raw materials:

2-C-methyl-D-ribono-1,4-lactone

Refernces

• 1、 Lopez-Herrera, F. J.,Sarabia-Garcia, F.,Pino-Gonzalez, M. S.,Garcia-Aranda, J. F.. "A NEW SYMTHESIS OF 2-C-METHYL-D-RIBONO-1,4-LACTONE AND THE C-9/C-13 FRAGMENT OF METHYNOLIDE". . p. 767 - 776. Retrieved 2007/10/02.