(1R,2R,5R,7R,8S)-5-(4,4'-dimethoxytrityloxymethyl)-8-hydroxy-2-methyl-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane

Base Information

Chemical Name:(1R,2R,5R,7R,8S)-5-(4,4'-dimethoxytrityloxymethyl)-8-hydroxy-2-methyl-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane
CAS No.:945383-24-4
Molecular Formula:C₃₅H₃₈N₂O₇
Molecular Weight:598.696
Hs Code.:

Synonyms:(1R,2R,5R,7R,8S)-5-(4,4'-dimethoxytrityloxymethyl)-8-hydroxy-2-methyl-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane

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Chemical Property of (1R,2R,5R,7R,8S)-5-(4,4'-dimethoxytrityloxymethyl)-8-hydroxy-2-methyl-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane

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Technology Process of (1R,2R,5R,7R,8S)-5-(4,4'-dimethoxytrityloxymethyl)-8-hydroxy-2-methyl-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane

There total 15 articles about (1R,2R,5R,7R,8S)-5-(4,4'-dimethoxytrityloxymethyl)-8-hydroxy-2-methyl-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]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: 80.0%

: 945383-22-2
(1R,2R,5R,7R,8S)-8-hydroxy-5-hydroxymethyl-2-methyl-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 945383-24-4
(1R,2R,5R,7R,8S)-5-(4,4'-dimethoxytrityloxymethyl)-8-hydroxy-2-methyl-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane

Guidance literature:: In pyridine; at 20 ℃;
DOI:10.1021/ja071106y

Reference yield:

: 945383-09-5
3,5-di-O-benzyl-4-C-hydroxypropyl-1,2-O-isopropylidene-α-D-ribofuranose

: 945383-24-4
(1R,2R,5R,7R,8S)-5-(4,4'-dimethoxytrityloxymethyl)-8-hydroxy-2-methyl-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 9 steps

1.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -78 - 20 °C

2.1: BuLi / tetrahydrofuran; hexane / -78 °C

2.2: 3.5 g / tetrahydrofuran; hexane

3.1: acetic acid; triflic acid / 0.5 h / ice bath

4.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating

4.2: TMSOTf / acetonitrile / 0 - 20 °C

5.1: 2.8 g / ammonia / methanol

6.1: 60 percent / DMAP; pyridine

7.1: Bu₃SnH / toluene / 0.25 h / Heating

7.2: 76 percent / 2,2'-azobis(2-methyl-propionitrile; Bu₃SnH / toluene / 2 h / Heating

8.1: 82 percent / ammonium formate / Pd(OH)2/C / methanol / Heating

9.1: 80 percent / pyridine / 20 °C

With pyridine; dmap; n-butyllithium; N,O-bis-(trimethylsilyl)-acetamide; oxalyl dichloride; trifluorormethanesulfonic acid; ammonia; tri-n-butyl-tin hydride; ammonium formate; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; toluene; acetonitrile; 1.1: Swern oxidation / 2.2: Wittig reaction / 4.2: Vorbrueggen reaction;
DOI:10.1021/ja071106y

Reference yield:

: 945383-16-4
1-[3,5-di-O-benzyl-4-C-penten-yl-2-hydroxy-β-D-ribofuranosyl]-thymine

: 945383-24-4
(1R,2R,5R,7R,8S)-5-(4,4'-dimethoxytrityloxymethyl)-8-hydroxy-2-methyl-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 60 percent / DMAP; pyridine

2.1: Bu₃SnH / toluene / 0.25 h / Heating

2.2: 76 percent / 2,2'-azobis(2-methyl-propionitrile; Bu₃SnH / toluene / 2 h / Heating

3.1: 82 percent / ammonium formate / Pd(OH)2/C / methanol / Heating

4.1: 80 percent / pyridine / 20 °C

With pyridine; dmap; tri-n-butyl-tin hydride; ammonium formate; palladium dihydroxide; In pyridine; methanol; toluene;
DOI:10.1021/ja071106y