(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

Base Information

Chemical Name:(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
CAS No.:485755-42-8
Molecular Formula:C₃₇H₃₆N₂O₉
Molecular Weight:652.701
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 10 articles about (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 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: 90.0%

: 485755-41-7
1-(2-O-acetyl-3-C-allyl-3,5-di-O-benzyl-4-C-(1(S)-(benzoyloxy)allyl)-β-D-ribofuranosyl)thymine

: 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

Guidance literature:: Grubbs catalyst first generation; In 1,2-dichloro-ethane;
DOI:10.1039/b205031e

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

: 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

Guidance literature:: Multi-step reaction with 2 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

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

Reference yield:

: 197702-06-0
3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 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

Guidance literature:: Multi-step reaction with 9 steps

1.1: H₅IO₆ / ethyl acetate

1.2: aq. NaOH / tetrahydrofuran

1.3: 82 percent / NaBH₄

2.1: 55 percent / NaH / dimethylformamide

3.1: PCC / CH₂Cl₂

4.1: tetrahydrofuran

5.1: 98 percent / pyridine

6.1: aq. AcOH / 90 °C

7.1: pyridine

8.1: 93 percent / N,O-bis(trimethylsilyl)acetamide; TMS-triflate / acetonitrile / 60 °C

9.1: 90 percent / Grubbs' catalyst / 1,2-dichloro-ethane

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium hydride; acetic acid; periodic acid; pyridinium chlorochromate; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; 4.1: Grignard addition;
DOI:10.1039/b205031e