N1-(3,5-di-O-benzyl-3-C-(methanesulfonyloxymethyl)-α-D-arabinofuranosyl)thymine

Base Information

Chemical Name:N1-(3,5-di-O-benzyl-3-C-(methanesulfonyloxymethyl)-α-D-arabinofuranosyl)thymine
CAS No.:858129-00-7
Molecular Formula:C₂₆H₃₀N₂O₉S
Molecular Weight:546.598
Hs Code.:

Synonyms:N1-(3,5-di-O-benzyl-3-C-(methanesulfonyloxymethyl)-α-D-arabinofuranosyl)thymine

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Chemical Property of N1-(3,5-di-O-benzyl-3-C-(methanesulfonyloxymethyl)-α-D-arabinofuranosyl)thymine

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Technology Process of N1-(3,5-di-O-benzyl-3-C-(methanesulfonyloxymethyl)-α-D-arabinofuranosyl)thymine

There total 15 articles about N1-(3,5-di-O-benzyl-3-C-(methanesulfonyloxymethyl)-α-D-arabinofuranosyl)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: 84.0%

: 858128-99-1
N1-(3,5-di-O-benzyl-3-C-(hydroxymethyl)-α-D-arabinofuranosyl)thymine

: 124-63-0
methanesulfonyl chloride

: 858129-00-7
N1-(3,5-di-O-benzyl-3-C-(methanesulfonyloxymethyl)-α-D-arabinofuranosyl)thymine

Guidance literature:: With pyridine; at -40 - 20 ℃; for 3h;
DOI:10.1021/jo0500380

Reference yield:

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

: 858129-00-7
N1-(3,5-di-O-benzyl-3-C-(methanesulfonyloxymethyl)-α-D-arabinofuranosyl)thymine

Guidance literature:: Multi-step reaction with 3 steps

1.1: 56 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 24 h / 70 °C

2.1: osmium tetraoxide; sodium periodate / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 18 h / 20 °C

2.2: 11 percent / sodium borohydride / tetrahydrofuran; H₂O / 1 h / 20 °C

3.1: 84 percent / pyridine / 3 h / -40 - 20 °C

With pyridine; sodium periodate; osmium(VIII) oxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo0500380

Reference yield:

: methyl 3,5-di-O-benzyl-3-C-vinyl-D-ribofuranoside

: 858129-00-7
N1-(3,5-di-O-benzyl-3-C-(methanesulfonyloxymethyl)-α-D-arabinofuranosyl)thymine

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine / CH₂Cl₂ / -30 - 20 °C

2.1: 682 mg / 18-crown-6 / dimethylformamide / 3 h / 95 °C

3.1: 56 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 24 h / 70 °C

4.1: osmium tetraoxide; sodium periodate / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 18 h / 20 °C

4.2: 11 percent / sodium borohydride / tetrahydrofuran; H₂O / 1 h / 20 °C

5.1: 84 percent / pyridine / 3 h / -40 - 20 °C

With pyridine; sodium periodate; osmium(VIII) oxide; N,O-bis-(trimethylsilyl)-acetamide; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo0500380