5-(Acetyloxy)-1,3-oxathiolane-2-Methanol Benzoate

Base Information

• Chemical Name: 5-(Acetyloxy)-1,3-oxathiolane-2-Methanol Benzoate
• CAS No.: 146726-76-3
• Molecular Formula: C₁₃H₁₄O₅S
• Molecular Weight: 282.317
• Mol file: 146726-76-3.mol

Synonyms:

Chemical Property of 5-(Acetyloxy)-1,3-oxathiolane-2-Methanol Benzoate

Chemical Property:

• Solubility.: Chloroform, DCM, DMSO, Methanol

Purity/Quality:

99.3% ^*data from raw suppliers

5-(Acetyloxy)-1,3-oxathiolane-2-methanolBenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 5-(Acetyloxy)-1,3-oxathiolane-2-methanol Benzoate is an intermediate used in the synthesis of antiviral nucleosides.

Technology Process of 5-(Acetyloxy)-1,3-oxathiolane-2-Methanol Benzoate

There total 16 articles about 5-(Acetyloxy)-1,3-oxathiolane-2-Methanol Benzoate 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: 90.0%

1,4-dithiane-2,5-diol (40018-26-6) + 2-benzoyloxyacetaldehyde (64904-47-8) + acetyl chloride (75-36-5) → 2-benzoyloxymethyl-5-acethoxy-1,3-oxathiolane (143919-90-8,143957-14-6,146726-76-3)

Guidance literature:

1,4-dithiane-2,5-diol; 2-benzoyloxyacetaldehyde; at 60 - 65 ℃; for 2h;

acetyl chloride; In dichloromethane; at 0 - 5 ℃; for 3h;

Reference yield: 64.0%

lead(IV) tetraacetate (546-67-8) + (2R,5S)-2-Benzoyloxymethyl-[1,3]oxathiolane-5-carboxylic acid (143957-11-3) → ((2R)-5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate (143919-90-8,143957-14-6,146726-76-3)

Guidance literature:

In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)61330-8

Reference yield:

acetic anhydride (108-24-7) + 2-Benzoyloxymethyl-1,3-oxathiolan-5-one (138760-37-9) → 2-benzoyloxymethyl-5-acethoxy-1,3-oxathiolane (143919-90-8,143957-14-6,146726-76-3)

Guidance literature:

2-Benzoyloxymethyl-1,3-oxathiolan-5-one; With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at -10 - 0 ℃; for 2h;

acetic anhydride; With dmap; In tetrahydrofuran; for 2h;

upstream raw materials:

lead(IV) tetraacetate

(2R,5S)-2-Benzoyloxymethyl-[1,3]oxathiolane-5-carboxylic acid

2-benzoyloxyacetaldehyde

1,4-dithiane-2,5-diol

Downstream raw materials:

cis/trans-2-benzoyloxymethyl-5-(cytosin-1'-yl)-1,3-oxathiolane

((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate

((2R)-5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate

lamivudine

Refernces

• 1、 -. "Preparation method for emtricitabine isomer". . . Retrieved 2019/04/26.
• 2、 -. "PROCESS FOR THE MANUFACTURE OF CIS(-)-LAMIVUDINE". Page/Page column 11. . Retrieved 2011/10/31.