(1S,3R,4R,5S,6S,8R,9R)-1-(benzyloxy)-6-[(benzyloxy)methyl]-3,4,5,9-tetrahydroxy-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]nonane

Base Information

Chemical Name:(1S,3R,4R,5S,6S,8R,9R)-1-(benzyloxy)-6-[(benzyloxy)methyl]-3,4,5,9-tetrahydroxy-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]nonane
CAS No.:696600-02-9
Molecular Formula:C₂₈H₃₂N₂O₉
Molecular Weight:540.57
Hs Code.:

Synonyms:(1S,3R,4R,5S,6S,8R,9R)-1-(benzyloxy)-6-[(benzyloxy)methyl]-3,4,5,9-tetrahydroxy-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]nonane

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Chemical Property of (1S,3R,4R,5S,6S,8R,9R)-1-(benzyloxy)-6-[(benzyloxy)methyl]-3,4,5,9-tetrahydroxy-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]nonane

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Technology Process of (1S,3R,4R,5S,6S,8R,9R)-1-(benzyloxy)-6-[(benzyloxy)methyl]-3,4,5,9-tetrahydroxy-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]nonane

There total 3 articles about (1S,3R,4R,5S,6S,8R,9R)-1-(benzyloxy)-6-[(benzyloxy)methyl]-3,4,5,9-tetrahydroxy-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]nonane 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: 75.0%

: 660847-65-4
(1S,3R,4R,5S,6S,8R,9R)-9-acetyloxy-5-(benzoyloxy)-1-(benzyloxy)-6-[(benzyloxy)methyl]-3,4-dihydroxy-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]nonane

: 696600-02-9
(1S,3R,4R,5S,6S,8R,9R)-1-(benzyloxy)-6-[(benzyloxy)methyl]-3,4,5,9-tetrahydroxy-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]nonane

Guidance literature:: With sodium methylate; In methanol; at 65 ℃; for 9h;
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

: 696600-02-9
(1S,3R,4R,5S,6S,8R,9R)-1-(benzyloxy)-6-[(benzyloxy)methyl]-3,4,5,9-tetrahydroxy-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]nonane

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: N-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 7 h / 50 °C

4: 75 percent / sodium methoxide / methanol / 9 h / 65 °C

With osmium(VIII) oxide; Grubbs catalyst first generation; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol; 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

: 696600-02-9
(1S,3R,4R,5S,6S,8R,9R)-1-(benzyloxy)-6-[(benzyloxy)methyl]-3,4,5,9-tetrahydroxy-8-(thymin-1-yl)-7-oxabicyclo[4.3.0]nonane

Guidance literature:: Multi-step reaction with 2 steps

1: N-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 7 h / 50 °C

2: 75 percent / sodium methoxide / methanol / 9 h / 65 °C

With osmium(VIII) oxide; sodium methylate; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; tert-butyl alcohol;
DOI:10.1016/j.tet.2004.03.019