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

Base Information

Chemical Name:(1R,3R,4R,7R)-7-benzyloxy-1-(hydroxymethyl)-3-(thymin-1-yl)-5-(trifluoroacetyl)-2-oxa-5-azabicyclo[2.2.1]heptane
CAS No.:861230-77-5
Molecular Formula:C₂₀H₂₀F₃N₃O₆
Molecular Weight:455.391
Hs Code.:

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

There total 11 articles about (1R,3R,4R,7R)-7-benzyloxy-1-(hydroxymethyl)-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: 93.0%

: 383-63-1
ethyl trifluoroacetate,

: 601512-87-2
(1R,3R,4R,7R)-7-benzyloxy-1-(hydroxymethyl)-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

: 861230-77-5
(1R,3R,4R,7R)-7-benzyloxy-1-(hydroxymethyl)-3-(thymin-1-yl)-5-(trifluoroacetyl)-2-oxa-5-azabicyclo[2.2.1]heptane

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

Reference yield:

: 601512-83-8
2,2'-anhydro-1-[3-O-benzyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-erythro-pentofuranosyl]thymine

: 861230-77-5
(1R,3R,4R,7R)-7-benzyloxy-1-(hydroxymethyl)-3-(thymin-1-yl)-5-(trifluoroacetyl)-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 6 steps

1.1: 98 percent / aq. H₂SO₄ / acetone / 14 h / Heating

2.1: trifluoromethanesulfonic anhydride; DMAP; pyridine / CH₂Cl₂ / 7 h / -78 - 0 °C

2.2: 3.5 g / NaN₃ / dimethylformamide / 18 h / 20 °C

3.1: 1.1 g / aq. NaOH; trimethylphosphane / tetrahydrofuran / 72 h / 20 °C

4.1: 15-crown-5 / dimethylformamide / 30 h / 120 °C

5.1: 0.5 g / NH₃ / methanol / 18 h / 20 °C

6.1: 93 percent / DMAP / methanol / 16 h / 20 °C

With pyridine; dmap; sodium hydroxide; 15-crown-5; sulfuric acid; ammonia; trifluoromethanesulfonic acid anhydride; trimethylphosphane; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; 5.1: Zemplen O-debenzoylation;
DOI:10.1002/ejoc.200500023

Reference yield:

: 601512-86-1
(1R,3R,4R,7R)-7-benzyloxy-1-(methylsulfonyloxymethyl)-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

: 861230-77-5
(1R,3R,4R,7R)-7-benzyloxy-1-(hydroxymethyl)-3-(thymin-1-yl)-5-(trifluoroacetyl)-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 3 steps

1: 15-crown-5 / dimethylformamide / 30 h / 120 °C

2: 0.5 g / NH₃ / methanol / 18 h / 20 °C

3: 93 percent / DMAP / methanol / 16 h / 20 °C

With dmap; 15-crown-5; ammonia; In methanol; N,N-dimethyl-formamide; 2: Zemplen O-debenzoylation;
DOI:10.1002/ejoc.200500023