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

Base Information

Chemical Name:2-Oxa-6-azabicyclo[3.2.0]heptane, 1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-6-(phenoxyacetyl)- 4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-, (1R,3R,4S,5R)-
CAS No.:874812-41-6
Molecular Formula:C33H33N3O7
Molecular Weight:583.641
Hs Code.:

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

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

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

There total 12 articles about 2-Oxa-6-azabicyclo[3.2.0]heptane, 1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-6-(phenoxyacetyl)- 4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-, (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: 86.0%

: 874812-40-5
(1R,3R,4S,5R)-3-benzyloxymethyl-4-benzyloxy-1-(thymin-1-yl)-6-aza-2-oxabicyclo[3.2.0]heptane

: 701-99-5
Phenoxyacetyl chloride

: 874812-41-6
(1R,3R,4S,5R)-3-benzyloxymethyl-4-benzyloxy-6-N-phenoxyacetyl-1-(thymin-1-yl)-6-aza-2-oxabicyclo[3.2.0]heptane

Guidance literature:: With pyridine; at 20 ℃; for 3h;
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

: 874812-41-6
(1R,3R,4S,5R)-3-benzyloxymethyl-4-benzyloxy-6-N-phenoxyacetyl-1-(thymin-1-yl)-6-aza-2-oxabicyclo[3.2.0]heptane

Guidance literature:: Multi-step reaction with 9 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

With pyridine; sodium hydroxide; ammonium cerium(IV) nitrate; sodium methylate; sodium hydride; triethylamine; methylamine; 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

: 874812-41-6
(1R,3R,4S,5R)-3-benzyloxymethyl-4-benzyloxy-6-N-phenoxyacetyl-1-(thymin-1-yl)-6-aza-2-oxabicyclo[3.2.0]heptane

Guidance literature:: Multi-step reaction with 8 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

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