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

Base Information

Chemical Name:(1R,3R,4R,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-5-(trifluoroacetyl)-2-oxa-5-azabicyclo[2.2.1]heptane
CAS No.:601512-90-7
Molecular Formula:C₃₄H₃₂F₃N₃O₈
Molecular Weight:667.639
Hs Code.:

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

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

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

There total 23 articles about (1R,3R,4R,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-5-(trifluoroacetyl)-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: 94.0%

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

: 601512-89-4
(1R,3R,4R,7R)-7-hydroxy-1-(hydroxymethyl)-3-(thymin-1-yl)-5-(trifluoroacetyl)-2-oxa-5-azabicyclo[2.2.1]heptane

: 601512-90-7
(1R,3R,4R,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-5-(trifluoroacetyl)-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: With pyridine; at 20 ℃;
DOI:10.1016/S0960-894X(03)00441-4

Reference yield:

: 410076-93-6
3-O-benzyl-1,2-di-O-acetyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α,β-L-threo-pentofuranose

: 601512-90-7
(1R,3R,4R,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-5-(trifluoroacetyl)-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 12 steps

1.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.67 h / Heating

1.2: 72 percent / TMS-triflate / acetonitrile / 3 h / Heating

2.1: 86 percent / diisopropylethylamine / CH₂Cl₂ / 44 h / 0 - 20 °C

3.1: 94 percent / NH₃ / methanol / 0.25 h / 0 - 20 °C

4.1: DMAP; pyridine; trifluoromethanesulfonic anhydride / CH₂Cl₂ / 4 h / 0 °C

4.2: 72 percent / aq. NaHCO₃ / CH₂Cl₂ / 0 - 20 °C

5.1: 70 percent / DMAP; pyridine / CH₂Cl₂ / 4 h / 0 °C

6.1: 83 percent / NaN₃ / dimethylformamide / 18 h / 20 °C

7.1: triphenylphosphane; pyridine / 20 h / 20 °C

7.2: 99 percent / aq. NH₃ / pyridine / 24 h / 20 °C

8.1: 92 percent / 15-crown-5 / dimethylformamide / 24 h / 120 °C

9.1: 93 percent / NH₃ / methanol / 20 h / 20 °C

10.1: 78 percent / DMAP / methanol / 4 h / 20 °C

11.1: BCl₃ / CH₂Cl₂ / 2 h / -78 - 20 °C

11.2: 91 percent / H₂O / 24 h / 20 °C

12.1: 94 percent / pyridine / 18 h / 20 °C

With pyridine; dmap; sodium azide; N,O-bis-(trimethylsilyl)-acetamide; 15-crown-5; ammonia; boron trichloride; trifluoromethanesulfonic acid anhydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 9.1: Zemplen O-debenzoylation;
DOI:10.1002/ejoc.200500023

Reference yield:

: 601512-74-7
1-[2-O-acetyl-3-O-benzyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-threo-pentofuranosyl]thymine

: 601512-90-7
(1R,3R,4R,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-5-(trifluoroacetyl)-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 11 steps

1.1: 86 percent / diisopropylethylamine / CH₂Cl₂ / 44 h / 0 - 20 °C

2.1: 94 percent / NH₃ / methanol / 0.25 h / 0 - 20 °C

3.1: DMAP; pyridine; trifluoromethanesulfonic anhydride / CH₂Cl₂ / 4 h / 0 °C

3.2: 72 percent / aq. NaHCO₃ / CH₂Cl₂ / 0 - 20 °C

4.1: 70 percent / DMAP; pyridine / CH₂Cl₂ / 4 h / 0 °C

5.1: 83 percent / NaN₃ / dimethylformamide / 18 h / 20 °C

6.1: triphenylphosphane; pyridine / 20 h / 20 °C

6.2: 99 percent / aq. NH₃ / pyridine / 24 h / 20 °C

7.1: 92 percent / 15-crown-5 / dimethylformamide / 24 h / 120 °C

8.1: 93 percent / NH₃ / methanol / 20 h / 20 °C

9.1: 78 percent / DMAP / methanol / 4 h / 20 °C

10.1: BCl₃ / CH₂Cl₂ / 2 h / -78 - 20 °C

10.2: 91 percent / H₂O / 24 h / 20 °C

11.1: 94 percent / pyridine / 18 h / 20 °C

With pyridine; dmap; sodium azide; 15-crown-5; ammonia; boron trichloride; trifluoromethanesulfonic acid anhydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In methanol; dichloromethane; N,N-dimethyl-formamide; 8.1: Zemplen O-debenzoylation;
DOI:10.1002/ejoc.200500023