(1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-methylsulfonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

Base Information

Chemical Name:(1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-methylsulfonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene
CAS No.:383191-80-8
Molecular Formula:C₂₇H₂₈N₂O₈S
Molecular Weight:540.594
Hs Code.:

Synonyms:(1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-methylsulfonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

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Chemical Property of (1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-methylsulfonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

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Technology Process of (1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-methylsulfonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

There total 1 articles about (1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-methylsulfonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene 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%

: 124-63-0
methanesulfonyl chloride

: 352422-92-5
(1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-hydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

: 383191-80-8
(1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-methylsulfonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

Guidance literature:: With pyridine; at 20 ℃; for 3h;
DOI:10.1039/b104438a

Reference yield: 85.0%

: 383191-80-8
(1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-methylsulfonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

: 383191-81-9
(1R,3R,4S,5R,8R)-5,8-Bis(benzyloxy)-4-hydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

Guidance literature:: With sodium hydroxide; In ethanol; for 16h; Heating;
DOI:10.1039/b104438a

Reference yield:

: 383191-80-8
(1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-methylsulfonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

: 383191-87-5
(1S,3S,4R,6R,7R,8R,9R)-8-Benzoyloxy-7,9-dihydroxy-4-(thymin-1-yl)-2,5-dioxatricyclo[4.2.1.0^3,7]nonane

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / aq. NaOH / ethanol / 16 h / Heating

2: 83 percent / aq. OsO₄; N-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 50 °C

3: 77 percent / pyridine / 48 h / 20 °C

4: 76 percent / DBU / acetonitrile / 22 h / 20 °C

5: 83 percent / pyridine / 1 h / 20 °C

6: 57 percent / H₂ / 20 percent Pd(OH)2/C / methanol / 64 h / 20 °C

With pyridine; sodium hydroxide; osmium(VIII) oxide; hydrogen; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; acetonitrile; tert-butyl alcohol;
DOI:10.1039/b104438a