(1S,3R,4S,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

Base Information

Chemical Name:(1S,3R,4S,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane
CAS No.:866611-96-3
Molecular Formula:C₃₂H₃₃N₃O₇
Molecular Weight:571.63
Hs Code.:

Synonyms:(1S,3R,4S,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

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Chemical Property of (1S,3R,4S,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

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Technology Process of (1S,3R,4S,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

There total 17 articles about (1S,3R,4S,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-2-oxa-5-azabicyclo[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: 72.0%

: 894430-46-7
(1S,3R,4S,7R)-7-benzyloxy-1-(4,4'-dimethoxytrityloxymethyl)-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

: 866611-96-3
(1S,3R,4S,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: With ammonium formate; palladium dihydroxide; In ethyl acetate; at 65 ℃; for 23h;
DOI:10.1021/jo060331f

Reference yield:

: 894430-43-4
(1S,3R,4S,7R)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

: 866611-96-3
(1S,3R,4S,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridine / CH₂Cl₂

1.2: KOAc; 18-C-6 / dioxane

1.3: 70 percent / NH₃ / methanol

2.1: 80 percent / NaBH₄ / ethanol

3.1: 70 percent / DMAP; pyridine

4.1: 70 percent / HCO₂NH₄ / Pd(OH)2/C / ethyl acetate

With pyridine; dmap; sodium tetrahydroborate; ammonium formate; palladium dihydroxide; In ethanol; dichloromethane; ethyl acetate;
DOI:10.1080/15257770500276866

Reference yield:

: 1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-methanesulfonoxymethyl-L-erythro-pentofuranosyl]thymine

: 866611-96-3
(1S,3R,4S,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 5 steps

1.1: P(CH₃)3; NaOH / tetrahydrofuran; H₂O

2.1: pyridine / CH₂Cl₂

2.2: KOAc; 18-C-6 / dioxane

2.3: 70 percent / NH₃ / methanol

3.1: 80 percent / NaBH₄ / ethanol

4.1: 70 percent / DMAP; pyridine

5.1: 70 percent / HCO₂NH₄ / Pd(OH)2/C / ethyl acetate

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; ammonium formate; trimethylphosphane; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate;
DOI:10.1080/15257770500276866