(1S,5S,6S,8R,9R)-5-(benzoyloxy)-1,9-dihydroxy-6-(hydroxymethyl)-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]non-3-ene

Base Information

Chemical Name:(1S,5S,6S,8R,9R)-5-(benzoyloxy)-1,9-dihydroxy-6-(hydroxymethyl)-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]non-3-ene
CAS No.:696599-78-7
Molecular Formula:C₂₁H₂₂N₂O₈
Molecular Weight:430.414
Hs Code.:

Synonyms:(1S,5S,6S,8R,9R)-5-(benzoyloxy)-1,9-dihydroxy-6-(hydroxymethyl)-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]non-3-ene

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Chemical Property of (1S,5S,6S,8R,9R)-5-(benzoyloxy)-1,9-dihydroxy-6-(hydroxymethyl)-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]non-3-ene

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Technology Process of (1S,5S,6S,8R,9R)-5-(benzoyloxy)-1,9-dihydroxy-6-(hydroxymethyl)-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]non-3-ene

There total 4 articles about (1S,5S,6S,8R,9R)-5-(benzoyloxy)-1,9-dihydroxy-6-(hydroxymethyl)-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]non-3-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: 55.0%

: 696599-72-1
(1S,5S,6S,8R,9R)-5-(benzoyloxy)-1-(benzyloxy)-6-[(benzyloxy)methyl]-9-hydroxy-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]non-3-ene

: 696599-78-7
(1S,5S,6S,8R,9R)-5-(benzoyloxy)-1,9-dihydroxy-6-(hydroxymethyl)-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]non-3-ene

Guidance literature:: With boron trichloride; In hexane; dichloromethane; at -78 - 20 ℃; for 20h;
DOI:10.1016/j.tet.2004.03.019

Reference yield:

: 485755-40-6
1,2-di-O-acetyl-3-C-allyl-3,5-di-O-benzyl-4-C-(1(S)-(benzoyloxy)allyl)-α/β-D-ribofuranose

: 696599-78-7
(1S,5S,6S,8R,9R)-5-(benzoyloxy)-1,9-dihydroxy-6-(hydroxymethyl)-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]non-3-ene

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / N,O-bis(trimethylsilyl)acetamide; TMS-OTf / acetonitrile / 17 h / 40 °C

2: 90 percent / Grubbs' catalyst / 1,2-dichloro-ethane / 25 h / Heating

3: 87 percent / sodium methoxide / methanol / 3 h / 20 °C

4: 55 percent / BCl₃ / CH₂Cl₂; hexane / 20 h / -78 - 20 °C

With Grubbs catalyst first generation; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; boron trichloride; In methanol; hexane; dichloromethane; 1,2-dichloro-ethane; acetonitrile; 1: Vorbrueggen coupling;
DOI:10.1016/j.tet.2004.03.019

Reference yield:

: 485755-42-8
(1S,5S,6S,8R,9R)-9-acetyloxy-5-(benzoyloxy)-1-(benzyloxy)-6-[(benzyloxy)methyl]-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]non-3-ene

: 696599-78-7
(1S,5S,6S,8R,9R)-5-(benzoyloxy)-1,9-dihydroxy-6-(hydroxymethyl)-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]non-3-ene

Guidance literature:: Multi-step reaction with 2 steps

1: 87 percent / sodium methoxide / methanol / 3 h / 20 °C

2: 55 percent / BCl₃ / CH₂Cl₂; hexane / 20 h / -78 - 20 °C

With sodium methylate; boron trichloride; In methanol; hexane; dichloromethane;
DOI:10.1016/j.tet.2004.03.019