(1S,3S,5R,6R,8R)-3-Acetoxymethyl-6-(4,4'-dimethoxytrityloxomethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

Base Information

Chemical Name:(1S,3S,5R,6R,8R)-3-Acetoxymethyl-6-(4,4'-dimethoxytrityloxomethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane
CAS No.:250222-72-1
Molecular Formula:C₃₆H₃₈N₂O₁₀
Molecular Weight:658.705
Hs Code.:

Synonyms:(1S,3S,5R,6R,8R)-3-Acetoxymethyl-6-(4,4'-dimethoxytrityloxomethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

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Chemical Property of (1S,3S,5R,6R,8R)-3-Acetoxymethyl-6-(4,4'-dimethoxytrityloxomethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

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Technology Process of (1S,3S,5R,6R,8R)-3-Acetoxymethyl-6-(4,4'-dimethoxytrityloxomethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

There total 10 articles about (1S,3S,5R,6R,8R)-3-Acetoxymethyl-6-(4,4'-dimethoxytrityloxomethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane 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: 96.0%

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

: 250222-70-9
(1S,3S,5R,6R,8R)-3-Acetoxymethyl-5-hydroxy-6-hydroxymethyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

: 250222-72-1
(1S,3S,5R,6R,8R)-3-Acetoxymethyl-6-(4,4'-dimethoxytrityloxomethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

Guidance literature:: With pyridine; for 15h;

Reference yield:

: 199931-09-4
1-(3-C-Allyl-3,5-di-O-benzyl-β-D-arabinofuranosyl)thymine

: 250222-72-1
(1S,3S,5R,6R,8R)-3-Acetoxymethyl-6-(4,4'-dimethoxytrityloxomethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / NMO; OsO₄; H₂O / tetrahydrofuran; 2-methyl-propan-2-ol / 15 h / 20 °C

2: 31 percent / pyridine / 12 h / 20 °C

3: pyridine / 72 h / 20 °C

4: K₂CO₃; 18-crown-6 / dimethylformamide / 24 h / 70 °C

5: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

6: 92 percent / pyridine / 15 h / 20 °C

7: 95 percent / H₂ / 20 percent Pd(OH)2/C / ethanol

8: 96 percent / pyridine / 15 h

With pyridine; osmium(VIII) oxide; N-methyl-2-indolinone; 18-crown-6 ether; tetrabutyl ammonium fluoride; water; hydrogen; potassium carbonate; palladium dihydroxide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Oxidation / 2: Etherification / 3: Tosylation / 4: Cyclization / 5: Desilylation / 6: Acetylation / 7: Hydrogenolysis / 8: Etherification;

Reference yield:

: 191163-58-3
1-(3-C-Allyl-3,5-di-O-benzyl-2-O-methylsulfonyl-β-D-ribofuranosyl)thymine

: 250222-72-1
(1S,3S,5R,6R,8R)-3-Acetoxymethyl-6-(4,4'-dimethoxytrityloxomethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 2 steps

1: 89 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 0 °C

2: 18 percent / MeONa / methanol / 6 h / 20 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; sodium methylate; In methanol; dichloromethane; 1: Oxidation / 2: Cycloaddition;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f