2-Oxa-6-azabicyclo[3.2.0]heptan-4-ol, 3-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-1-(3,4-dihydro-5-methyl -2,4-dioxo-1(2H)-pyrimidinyl)-6-(phenoxyacetyl)-, (1R,3R,4S,5R)-

Base Information

Chemical Name:2-Oxa-6-azabicyclo[3.2.0]heptan-4-ol, 3-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-1-(3,4-dihydro-5-methyl -2,4-dioxo-1(2H)-pyrimidinyl)-6-(phenoxyacetyl)-, (1R,3R,4S,5R)-
CAS No.:874812-43-8
Molecular Formula:C40H39N3O9
Molecular Weight:705.764
Hs Code.:

2-Oxa-6-azabicyclo[3.2.0]heptan-4-ol,
3-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-1-(3,4-dihydro-5-methyl
-2,4-dioxo-1(2H)-pyrimidinyl)-6-(phenoxyacetyl)-, (1R,3R,4S,5R)-

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Chemical Property of 2-Oxa-6-azabicyclo[3.2.0]heptan-4-ol, 3-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-1-(3,4-dihydro-5-methyl -2,4-dioxo-1(2H)-pyrimidinyl)-6-(phenoxyacetyl)-, (1R,3R,4S,5R)-

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Technology Process of 2-Oxa-6-azabicyclo[3.2.0]heptan-4-ol, 3-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-1-(3,4-dihydro-5-methyl -2,4-dioxo-1(2H)-pyrimidinyl)-6-(phenoxyacetyl)-, (1R,3R,4S,5R)-

There total 13 articles about 2-Oxa-6-azabicyclo[3.2.0]heptan-4-ol, 3-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-1-(3,4-dihydro-5-methyl -2,4-dioxo-1(2H)-pyrimidinyl)-6-(phenoxyacetyl)-, (1R,3R,4S,5R)- 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: 73.0%

: 874812-42-7
1-[(1R,3R,4S,5R)-4-Hydroxy-3-hydroxymethyl-6-(2-phenoxy-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-1-yl]-5-methyl-1H-pyrimidine-2,4-dione

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 874812-43-8
(1R,3R,4S,5R)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-6-N-phenoxyacetyl-1-(thymin-1-yl)-6-aza-2-oxabicyclo[3.2.0]heptane

Guidance literature:: With pyridine; at 20 ℃;
DOI:10.1021/jo052115x

Reference yield:

: 1054657-53-2
(2R,3R,3aS,9aR)-3-Benzyloxy-2-benzyloxymethyl-9a-hydroxymethyl-7-methyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one

: 874812-43-8
(1R,3R,4S,5R)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-6-N-phenoxyacetyl-1-(thymin-1-yl)-6-aza-2-oxabicyclo[3.2.0]heptane

Guidance literature:: Multi-step reaction with 11 steps

1.1: 3.26 g / aq. NaOH / ethanol / 20 °C

2.1: 98 percent / pyridine / 3 h / 20 °C

3.1: 80 percent / NaH / dimethylformamide / 0 - 20 °C

4.1: 94 percent / MeONa / methanol / 0.5 h / 20 °C

5.1: pyridine / 0 - 4 °C

5.2: 77 percent / dimethylformamide / 110 °C

6.1: 93 percent / aq. MeNH₂ / methanol / 4 h / 20 °C

7.1: 66 percent / Et₃N; pyridine / 48 h / 90 °C

8.1: 62 percent / ceric ammonium nitrate / acetonitrile; H₂O / 3 h / 20 °C

9.1: 86 percent / pyridine / 3 h / 20 °C

10.1: 92 percent / ammonium formate / Pd(OH)2/C / methanol / 3 h / Heating

11.1: 73 percent / pyridine / 20 °C

With pyridine; sodium hydroxide; ammonium cerium(IV) nitrate; sodium methylate; ammonium formate; sodium hydride; triethylamine; methylamine; palladium dihydroxide; In methanol; ethanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo052115x

Reference yield:

: 874812-33-6
1-((2R,3S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-3-hydroxy-2-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

: 874812-43-8
(1R,3R,4S,5R)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-6-N-phenoxyacetyl-1-(thymin-1-yl)-6-aza-2-oxabicyclo[3.2.0]heptane

Guidance literature:: Multi-step reaction with 10 steps

1.1: 98 percent / pyridine / 3 h / 20 °C

2.1: 80 percent / NaH / dimethylformamide / 0 - 20 °C

3.1: 94 percent / MeONa / methanol / 0.5 h / 20 °C

4.1: pyridine / 0 - 4 °C

4.2: 77 percent / dimethylformamide / 110 °C

5.1: 93 percent / aq. MeNH₂ / methanol / 4 h / 20 °C

6.1: 66 percent / Et₃N; pyridine / 48 h / 90 °C

7.1: 62 percent / ceric ammonium nitrate / acetonitrile; H₂O / 3 h / 20 °C

8.1: 86 percent / pyridine / 3 h / 20 °C

9.1: 92 percent / ammonium formate / Pd(OH)2/C / methanol / 3 h / Heating

10.1: 73 percent / pyridine / 20 °C

With pyridine; ammonium cerium(IV) nitrate; sodium methylate; ammonium formate; sodium hydride; triethylamine; methylamine; palladium dihydroxide; In methanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo052115x