(1S,3S,4S)-3-(methanesulfonyloxymethyl)-5-N-(4-monomethoxytrityl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane

Base Information

Chemical Name:(1S,3S,4S)-3-(methanesulfonyloxymethyl)-5-N-(4-monomethoxytrityl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane
CAS No.:358625-72-6
Molecular Formula:C₃₁H₃₁N₃O₇S
Molecular Weight:589.669
Hs Code.:

Synonyms:(1S,3S,4S)-3-(methanesulfonyloxymethyl)-5-N-(4-monomethoxytrityl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane

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Chemical Property of (1S,3S,4S)-3-(methanesulfonyloxymethyl)-5-N-(4-monomethoxytrityl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane

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Technology Process of (1S,3S,4S)-3-(methanesulfonyloxymethyl)-5-N-(4-monomethoxytrityl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane

There total 5 articles about (1S,3S,4S)-3-(methanesulfonyloxymethyl)-5-N-(4-monomethoxytrityl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane 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: 80.0%

: 14470-28-1
mono-4-methoxytrityl chloride

: 358625-67-9
(1S,3S,4S)-3-(methanesulfonyloxymethyl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane

: 358625-72-6
(1S,3S,4S)-3-(methanesulfonyloxymethyl)-5-N-(4-monomethoxytrityl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane

Guidance literature:: With pyridine; for 21h;
DOI:10.1021/jo015602v

Reference yield:

: 55697-37-5
1-(3'-deoxy-β-D-psicofuranosyl)uracil

: 358625-72-6
(1S,3S,4S)-3-(methanesulfonyloxymethyl)-5-N-(4-monomethoxytrityl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 8 steps

1.1: 77 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

2.1: 93 percent / pyridine / 2 h / 0 °C

3.1: 80 percent / sodium hydride / dimethylformamide / 72 h / 20 °C

4.1: 26 percent / sodium azide / dimethylformamide / 23 h / 120 °C

5.1: 81 percent / acetic acid / CH₂Cl₂; H₂O / 4 h

6.1: 92 percent / pyridine / 1.5 h / 0 °C

7.1: hydrogen / Pd/C / CH₂Cl₂; methanol / 25 h

7.2: 724 mg / dimethylformamide / 19 h / 60 °C

8.1: 80 percent / pyridine / 21 h

With pyridine; sodium azide; hydrogen; sodium hydride; acetic acid; palladium on activated charcoal; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo015602v

Reference yield:

: 358625-55-5
1-[4'-azido-3'-deoxy-β-D-psicofuranosyl]uracil

: 358625-72-6
(1S,3S,4S)-3-(methanesulfonyloxymethyl)-5-N-(4-monomethoxytrityl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 92 percent / pyridine / 1.5 h / 0 °C

2.1: hydrogen / Pd/C / CH₂Cl₂; methanol / 25 h

2.2: 724 mg / dimethylformamide / 19 h / 60 °C

3.1: 80 percent / pyridine / 21 h

With pyridine; hydrogen; palladium on activated charcoal; In methanol; dichloromethane;
DOI:10.1021/jo015602v