(1R,3R,4S,5R)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-1-(4-N-isobutyrylcytosin-1-yl)-6-N-phenoxyacetyl-6-aza-2-oxabicyclo[3.2.0]heptane

Base Information

Chemical Name:(1R,3R,4S,5R)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-1-(4-N-isobutyrylcytosin-1-yl)-6-N-phenoxyacetyl-6-aza-2-oxabicyclo[3.2.0]heptane
CAS No.:874812-60-9
Molecular Formula:C₄₃H₄₄N₄O₉
Molecular Weight:760.844
Hs Code.:

Synonyms:(1R,3R,4S,5R)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-1-(4-N-isobutyrylcytosin-1-yl)-6-N-phenoxyacetyl-6-aza-2-oxabicyclo[3.2.0]heptane

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Chemical Property of (1R,3R,4S,5R)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-1-(4-N-isobutyrylcytosin-1-yl)-6-N-phenoxyacetyl-6-aza-2-oxabicyclo[3.2.0]heptane

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Technology Process of (1R,3R,4S,5R)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-1-(4-N-isobutyrylcytosin-1-yl)-6-N-phenoxyacetyl-6-aza-2-oxabicyclo[3.2.0]heptane

There total 18 articles about (1R,3R,4S,5R)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-1-(4-N-isobutyrylcytosin-1-yl)-6-N-phenoxyacetyl-6-aza-2-oxabicyclo[3.2.0]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: 83.0%

: 874812-59-6
(1R,3R,4S,5R)-1-(cytosin-1-yl)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-6-N-(phenoxyacetyl)-6-aza-2-oxabicyclo[3.2.0]heptane

: 79-30-1
isobutyryl chloride

: 874812-60-9
(1R,3R,4S,5R)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-1-(4-N-isobutyrylcytosin-1-yl)-6-N-phenoxyacetyl-6-aza-2-oxabicyclo[3.2.0]heptane

Guidance literature:: (1R,3R,4S,5R)-1-(cytosin-1-yl)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-6-N-(phenoxyacetyl)-6-aza-2-oxabicyclo[3.2.0]heptane; With pyridine; chloro-trimethyl-silane; for 0.5h;

isobutyryl chloride; With pyridine; at 20 ℃; for 3h;
DOI:10.1021/jo052115x

Reference yield:

: 1-((2R,3R,4S,5R)-5-Benzyloxymethyl-3,4-dihydroxy-2-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

: 874812-60-9
(1R,3R,4S,5R)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-1-(4-N-isobutyrylcytosin-1-yl)-6-N-phenoxyacetyl-6-aza-2-oxabicyclo[3.2.0]heptane

Guidance literature:: Multi-step reaction with 17 steps

1.1: 3.1 g / pyridine / 24 h / 20 °C

2.1: 91 percent / diphenyl carbonate; NaHCO₃ / dimethylformamide / 2 h / 110 °C

3.1: 85 percent / NaH / acetonitrile / 0 - 20 °C

4.1: 79 percent / aq. AcOH / 48 h / 20 °C

5.1: 89 percent / pyridine / 1.5 h / 0 °C

6.1: 87 percent / NaN₃ / dimethylformamide / 60 h / 100 °C

7.1: 85 percent / aq. NaOH / ethanol; tetrahydrofuran / 2 h / 20 °C

8.1: 90 percent / pyridine / 24 h / 0 °C

9.1: 90 percent / PMe₃; H₂O / tetrahydrofuran / 1 h / 20 °C

10.1: 63 percent / pyridine; Et₃N / 48 h / 90 °C

11.1: 84 percent / pyridine / 2.5 h / 20 °C

12.1: BCl₃ / CH₂Cl₂ / -78 - 20 °C

13.1: 1.85 g / pyridine; DMAP / 5 h / 20 °C

14.1: pyridine / 24 h / 20 °C

15.1: 2-chlorophenylphosphorodichloridate; pyridine / 0 - 20 °C

16.1: 0.93 mmol / aq. NH₃; pyridine / 5 °C

17.1: ClSiMe₃; pyridine / 0.5 h

17.2: 83 percent / pyridine / 3 h / 20 °C

With pyridine; bis(phenyl) carbonate; dmap; ammonium hydroxide; sodium hydroxide; chloro-trimethyl-silane; sodium azide; water; boron trichloride; sodium hydride; sodium hydrogencarbonate; acetic acid; triethylamine; 2-chlorophenyl dichlorophosphate; trimethylphosphane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo052115x

Reference yield:

: 874812-49-4
(2R,3R,3aS,9aR)-3-Benzyloxy-2-benzyloxymethyl-9a-hydroxymethyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one

: 874812-60-9
(1R,3R,4S,5R)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-1-(4-N-isobutyrylcytosin-1-yl)-6-N-phenoxyacetyl-6-aza-2-oxabicyclo[3.2.0]heptane

Guidance literature:: Multi-step reaction with 13 steps

1.1: 89 percent / pyridine / 1.5 h / 0 °C

2.1: 87 percent / NaN₃ / dimethylformamide / 60 h / 100 °C

3.1: 85 percent / aq. NaOH / ethanol; tetrahydrofuran / 2 h / 20 °C

4.1: 90 percent / pyridine / 24 h / 0 °C

5.1: 90 percent / PMe₃; H₂O / tetrahydrofuran / 1 h / 20 °C

6.1: 63 percent / pyridine; Et₃N / 48 h / 90 °C

7.1: 84 percent / pyridine / 2.5 h / 20 °C

8.1: BCl₃ / CH₂Cl₂ / -78 - 20 °C

9.1: 1.85 g / pyridine; DMAP / 5 h / 20 °C

10.1: pyridine / 24 h / 20 °C

11.1: 2-chlorophenylphosphorodichloridate; pyridine / 0 - 20 °C

12.1: 0.93 mmol / aq. NH₃; pyridine / 5 °C

13.1: ClSiMe₃; pyridine / 0.5 h

13.2: 83 percent / pyridine / 3 h / 20 °C

With pyridine; dmap; ammonium hydroxide; sodium hydroxide; chloro-trimethyl-silane; sodium azide; water; boron trichloride; triethylamine; 2-chlorophenyl dichlorophosphate; trimethylphosphane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo052115x