(1S,3R,4S,5R)-4-[2-cyanoethoxy(diisopropylamino)-phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-(thymin-1-yl)-2,6-dioxabicyclo[3.2.0]heptane

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Chemical Name:(1S,3R,4S,5R)-4-[2-cyanoethoxy(diisopropylamino)-phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-(thymin-1-yl)-2,6-dioxabicyclo[3.2.0]heptane
CAS No.:904664-38-6
Molecular Formula:C₄₁H₄₉N₄O₉P
Molecular Weight:772.835
Hs Code.:

Synonyms:(1S,3R,4S,5R)-4-[2-cyanoethoxy(diisopropylamino)-phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-(thymin-1-yl)-2,6-dioxabicyclo[3.2.0]heptane

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Chemical Property of (1S,3R,4S,5R)-4-[2-cyanoethoxy(diisopropylamino)-phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-(thymin-1-yl)-2,6-dioxabicyclo[3.2.0]heptane

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Technology Process of (1S,3R,4S,5R)-4-[2-cyanoethoxy(diisopropylamino)-phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-(thymin-1-yl)-2,6-dioxabicyclo[3.2.0]heptane

There total 6 articles about (1S,3R,4S,5R)-4-[2-cyanoethoxy(diisopropylamino)-phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-(thymin-1-yl)-2,6-dioxabicyclo[3.2.0]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: 58.0%

: 904664-37-5
(1S,3R,4S,5R)-1-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-3-(thymin-1-yl)-2,6-dioxabicyclo[3.2.0]heptane

: 124482-92-4,89992-70-1
2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

: 904664-38-6
(1S,3R,4S,5R)-4-[2-cyanoethoxy(diisopropylamino)-phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-(thymin-1-yl)-2,6-dioxabicyclo[3.2.0]heptane

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 31h;
DOI:10.1016/j.carres.2006.04.010

Reference yield:

: 601512-84-9
1-[3-O-benzyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-erythro-pentofuranosyl]thymine

: 904664-38-6
(1S,3R,4S,5R)-4-[2-cyanoethoxy(diisopropylamino)-phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-(thymin-1-yl)-2,6-dioxabicyclo[3.2.0]heptane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 92 percent / H₂ / Pd(OH)2/C / ethyl acetate / 7 h / 20 °C

2.1: NaOH / H₂O / 22 h / 0 - 4 °C

2.2: 25 percent / dimethylformamide / 37 h / 60 - 75 °C

3.1: 84 percent / NH₃ / methanol / 28 h / 20 °C

4.1: 85 percent / pyridine / 2.83 h / 20 °C

5.1: 58 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 31 h / 20 °C

With sodium hydroxide; ammonia; hydrogen; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In pyridine; methanol; dichloromethane; water; ethyl acetate;
DOI:10.1016/j.carres.2006.04.010

Reference yield:

: 904664-36-4
(1S,3R,4S,5R)-4-hydroxy-1-hydroxymethyl-3-(thymin-1-yl)-2,6-dioxabicyclo[3.2.0]heptane

: 904664-38-6
(1S,3R,4S,5R)-4-[2-cyanoethoxy(diisopropylamino)-phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-(thymin-1-yl)-2,6-dioxabicyclo[3.2.0]heptane

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / pyridine / 2.83 h / 20 °C

2: 58 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 31 h / 20 °C

With N-ethyl-N,N-diisopropylamine; In pyridine; dichloromethane;
DOI:10.1016/j.carres.2006.04.010