(1R,3R,4R,5R,6S,7S,8R)-5,8-dibenzyloxy-4,6,7-trihydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane

Base Information

Chemical Name:(1R,3R,4R,5R,6S,7S,8R)-5,8-dibenzyloxy-4,6,7-trihydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane
CAS No.:557099-59-9
Molecular Formula:C₂₆H₂₈N₂O₈
Molecular Weight:496.517
Hs Code.:

Synonyms:(1R,3R,4R,5R,6S,7S,8R)-5,8-dibenzyloxy-4,6,7-trihydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane

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Chemical Property of (1R,3R,4R,5R,6S,7S,8R)-5,8-dibenzyloxy-4,6,7-trihydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane

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Technology Process of (1R,3R,4R,5R,6S,7S,8R)-5,8-dibenzyloxy-4,6,7-trihydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane

There total 5 articles about (1R,3R,4R,5R,6S,7S,8R)-5,8-dibenzyloxy-4,6,7-trihydroxy-3-(thymin-1-yl)-2-oxabicyclo[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: 95.0%

: 557099-58-8
(1R,3R,4R,5R,6S,7S,8R)-4,6,7-triacetyloxy-5,8-dibenzyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane

: 557099-59-9
(1R,3R,4R,5R,6S,7S,8R)-5,8-dibenzyloxy-4,6,7-trihydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 16h;
DOI:10.1039/b210439c

Reference yield:

: 557099-55-5
(1R,3R,7R,8R,9S,10S,11R)-8,11-dibenzyloxy-9,10-dihydroxy-5,5-dimethyl-2,4,6-trioxatricyclo[6.3.0.0^3,7]undecane

: 557099-59-9
(1R,3R,4R,5R,6S,7S,8R)-5,8-dibenzyloxy-4,6,7-trihydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 5 steps

1: 76 percent / pyridine / 16 h / 20 °C

2: aq. AcOH / 16 h / 90 °C

3: 200 mg / pyridine / 16 h

4: 65 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 16 h / 50 °C

5: 95 percent / NaOMe / methanol / 16 h / 20 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; acetic acid; In methanol; acetonitrile;
DOI:10.1039/b210439c

Reference yield:

: Acetic acid (3R,3aS,4S,5S,6R,6aR)-5-acetoxy-3a,6-bis-benzyloxy-2,3-dihydroxy-hexahydro-cyclopenta[b]furan-4-yl ester

: 557099-59-9
(1R,3R,4R,5R,6S,7S,8R)-5,8-dibenzyloxy-4,6,7-trihydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 3 steps

1: 200 mg / pyridine / 16 h

2: 65 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 16 h / 50 °C

3: 95 percent / NaOMe / methanol / 16 h / 20 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In methanol; acetonitrile;
DOI:10.1039/b210439c