(5aR,7R,8S,8aS)-8-(4,4'-dimethoxytrityloxymethyl)-5a,7,8,8a-tetrahydro-7-hydroxy-1H,6H-cyclopenta[4,5]oxazolo[3,2-c]pyrimidine-2,4(3H)-dione

Base Information

Chemical Name:(5aR,7R,8S,8aS)-8-(4,4'-dimethoxytrityloxymethyl)-5a,7,8,8a-tetrahydro-7-hydroxy-1H,6H-cyclopenta[4,5]oxazolo[3,2-c]pyrimidine-2,4(3H)-dione
CAS No.:670276-00-3
Molecular Formula:C₃₁H₃₀N₂O₇
Molecular Weight:542.588
Hs Code.:

Synonyms:(5aR,7R,8S,8aS)-8-(4,4'-dimethoxytrityloxymethyl)-5a,7,8,8a-tetrahydro-7-hydroxy-1H,6H-cyclopenta[4,5]oxazolo[3,2-c]pyrimidine-2,4(3H)-dione

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Chemical Property of (5aR,7R,8S,8aS)-8-(4,4'-dimethoxytrityloxymethyl)-5a,7,8,8a-tetrahydro-7-hydroxy-1H,6H-cyclopenta[4,5]oxazolo[3,2-c]pyrimidine-2,4(3H)-dione

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Technology Process of (5aR,7R,8S,8aS)-8-(4,4'-dimethoxytrityloxymethyl)-5a,7,8,8a-tetrahydro-7-hydroxy-1H,6H-cyclopenta[4,5]oxazolo[3,2-c]pyrimidine-2,4(3H)-dione

There total 6 articles about (5aR,7R,8S,8aS)-8-(4,4'-dimethoxytrityloxymethyl)-5a,7,8,8a-tetrahydro-7-hydroxy-1H,6H-cyclopenta[4,5]oxazolo[3,2-c]pyrimidine-2,4(3H)-dione 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: 94.1%

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

: 263764-09-6
(5aR,7R,8S,8aS)-5a,7,8,8a-tetrahydro-7-hydroxy-8-hydroxymethyl-2H,6H-cyclopenta[4,5]oxazolo[3,2-c]pyrimidine-2,4(3H)-dione

: 670276-00-3
(5aR,7R,8S,8aS)-8-(4,4'-dimethoxytrityloxymethyl)-5a,7,8,8a-tetrahydro-7-hydroxy-1H,6H-cyclopenta[4,5]oxazolo[3,2-c]pyrimidine-2,4(3H)-dione

Guidance literature:: With pyridine; at 20 ℃; for 2h;
DOI:10.1039/b312276j

Reference yield:

: 869749-13-3
(5aR,7R,8S,8aS)-7-benzyloxy-8-benzyloxymethyl-5a,7,8,8a-tetrahydro-2H,6H-cyclopenta[4,5]oxazolo[3,2-a]pyrimidine-2-one

: 670276-00-3
(5aR,7R,8S,8aS)-8-(4,4'-dimethoxytrityloxymethyl)-5a,7,8,8a-tetrahydro-7-hydroxy-1H,6H-cyclopenta[4,5]oxazolo[3,2-c]pyrimidine-2,4(3H)-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 93.4 percent / aq. NaOH / Heating

2: 91.4 percent / NBS; NaN₃ / 1,2-dimethoxy-ethane / 20 °C

3: 96.8 percent / DBU / dioxane / Heating

4: 72.1 percent / cyclohexene / Pd(OH)2/C / ethanol / Heating

5: 94.1 percent / pyridine / 2 h / 20 °C

With pyridine; sodium hydroxide; N-Bromosuccinimide; sodium azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; cyclohexene; palladium dihydroxide; In 1,4-dioxane; 1,2-dimethoxyethane; ethanol;
DOI:10.1039/b312276j

Reference yield:

: (1'R,2'R,3'R,4'R)-1-(4-benzyloxy-3-benzyloxymethyl-2-hydroxycyclopentyl)uracil

: 670276-00-3
(5aR,7R,8S,8aS)-8-(4,4'-dimethoxytrityloxymethyl)-5a,7,8,8a-tetrahydro-7-hydroxy-1H,6H-cyclopenta[4,5]oxazolo[3,2-c]pyrimidine-2,4(3H)-dione

Guidance literature:: Multi-step reaction with 6 steps

1: 85.2 percent / DEAD; Ph₃P / tetrahydrofuran / 20 °C

2: 93.4 percent / aq. NaOH / Heating

3: 91.4 percent / NBS; NaN₃ / 1,2-dimethoxy-ethane / 20 °C

4: 96.8 percent / DBU / dioxane / Heating

5: 72.1 percent / cyclohexene / Pd(OH)2/C / ethanol / Heating

6: 94.1 percent / pyridine / 2 h / 20 °C

With pyridine; sodium hydroxide; N-Bromosuccinimide; sodium azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; cyclohexene; diethylazodicarboxylate; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethanol;
DOI:10.1039/b312276j