1-(2-O-acetyl-3,5-di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-α-D-ribofuranosyl)thymine

Base Information

Chemical Name:1-(2-O-acetyl-3,5-di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-α-D-ribofuranosyl)thymine
CAS No.:209968-87-6
Molecular Formula:C₃₄H₃₆N₂O₁₀S
Molecular Weight:664.733
Hs Code.:

Synonyms:1-(2-O-acetyl-3,5-di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-α-D-ribofuranosyl)thymine

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Chemical Property of 1-(2-O-acetyl-3,5-di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-α-D-ribofuranosyl)thymine

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Technology Process of 1-(2-O-acetyl-3,5-di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-α-D-ribofuranosyl)thymine

There total 4 articles about 1-(2-O-acetyl-3,5-di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-α-D-ribofuranosyl)thymine 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: 94.0%

: 65-71-4,28806-14-6,691841-57-3
thymin

: 209968-86-5
4-C-[(phenylmethoxy)methyl]-3-O-(phenylmethyl)-1,2-diacetate 5-(4-methylbenzenesulfonate)-L-lyxofuranose

: 209968-87-6
1-(2-O-acetyl-3,5-di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-α-D-ribofuranosyl)thymine

Guidance literature:: thymin; 4-C-[(phenylmethoxy)methyl]-3-O-(phenylmethyl)-1,2-diacetate 5-(4-methylbenzenesulfonate)-L-lyxofuranose; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; for 3h; Heating;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; Further stages.; Heating;
DOI:10.1021/ja710342q

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 209968-87-6
1-(2-O-acetyl-3,5-di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-α-D-ribofuranosyl)thymine

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂

2: 80percent aq. AcOH

3: pyridine

4: 92 percent / N,O-bis(trimethylsilyl)acetamide, trimethylsilyl triflate / acetonitrile

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; acetic acid; In dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(98)00706-0

Reference yield:

: 153186-13-1
3,5-di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-1,2-O-isopropylidene-α-D-ribofuranose

: 209968-87-6
1-(2-O-acetyl-3,5-di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-α-D-ribofuranosyl)thymine

Guidance literature:: Multi-step reaction with 3 steps

1: 80percent aq. AcOH

2: pyridine

3: 92 percent / N,O-bis(trimethylsilyl)acetamide, trimethylsilyl triflate / acetonitrile

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; acetic acid; In acetonitrile;
DOI:10.1016/S0040-4039(98)00706-0