(1S,3S,5R,6R,8R)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxymethyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

Base Information

Chemical Name:(1S,3S,5R,6R,8R)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxymethyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane
CAS No.:250222-62-9
Molecular Formula:C₂₇H₃₀N₂O₇
Molecular Weight:494.544
Hs Code.:

Synonyms:(1S,3S,5R,6R,8R)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxymethyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

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Chemical Property of (1S,3S,5R,6R,8R)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxymethyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

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Technology Process of (1S,3S,5R,6R,8R)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxymethyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

There total 7 articles about (1S,3S,5R,6R,8R)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxymethyl-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: 94.0%

: 250222-64-1
(1S,3S,5R,6R,8R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyldimethylsilyloxymethyl)-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

: 250222-62-9
(1S,3S,5R,6R,8R)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxymethyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;

Reference yield:

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

: 250222-62-9
(1S,3S,5R,6R,8R)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxymethyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / NMO; OsO₄; H₂O / tetrahydrofuran; 2-methyl-propan-2-ol / 7 h / 20 °C

2: 98 percent / NaOH; H₂O / ethanol / 15 h / Heating

3: 31 percent / pyridine / 12 h / 20 °C

4: pyridine / 72 h / 20 °C

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

6: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

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

Reference yield:

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

: 250222-62-9
(1S,3S,5R,6R,8R)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxymethyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 5 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

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