(1S,5R,6R,8R)-6-(4,4'-Dimethoxytrityloxymethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

Base Information

• Chemical Name: (1S,5R,6R,8R)-6-(4,4'-Dimethoxytrityloxymethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane
• CAS No.: 191163-55-0
• Molecular Formula: C₃₃H₃₄N₂O₈
• Molecular Weight: 586.642
• Mol file: 191163-55-0.mol

Synonyms:(1S,5R,6R,8R)-6-(4,4'-Dimethoxytrityloxymethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

Chemical Property of (1S,5R,6R,8R)-6-(4,4'-Dimethoxytrityloxymethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5R,6R,8R)-6-(4,4'-Dimethoxytrityloxymethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

There total 20 articles about (1S,5R,6R,8R)-6-(4,4'-Dimethoxytrityloxymethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[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: 97.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + (1S,5R,6R,8R)-5-Hydroxy-6-hydroxymethyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane (191163-51-6) → (1S,5R,6R,8R)-6-(4,4'-Dimethoxytrityloxymethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane (191163-55-0)

Guidance literature:

With pyridine;

DOI:10.1039/a608231i

Reference yield:

5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose (103931-45-9) → (1S,5R,6R,8R)-6-(4,4'-Dimethoxytrityloxymethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane (191163-55-0)

Guidance literature:

Multi-step reaction with 16 steps

1: tetrahydrofuran; diethyl ether / 2 h / 0 °C

2: TBAF / tetrahydrofuran / 1 h / Ambient temperature

3: 86 percent / NaH / dimethylformamide / 1.) 50 deg C, 1 h, 2.) r.t., 18 h

4: aq. AcOH / 3 h / 90 °C

5: pyridine / 48 h / Ambient temperature

6: 86 percent / BSA, TMS triflate / acetonitrile / 1.) reflux, 1 h, 2.) r.t., 12 h

7: 95 percent / CH₃ONa / methanol / 16 h / Ambient temperature

8: 89 percent / pyridine / 1 h / Ambient temperature

9: aq. NaOH / 18 h / Heating

10: aq. NaHCO₃ / CH₂Cl₂

11: aq. NaIO₄, OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / Ambient temperature

12: aq. NaBH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

13: pyridine / 20 h / Ambient temperature

14: NaH / dimethylformamide / 18 h / 0 °C

15: 82 percent / H₂ / 20percent Pd(OH)2/C / ethanol / 2 h / Ambient temperature

16: 97 percent / pyridine / 5 h / Ambient temperature

With pyridine; benzenesulfonamide; sodium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; sodium hydride; sodium hydrogencarbonate; acetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

Reference yield:

[(2R,3S,4S,5R)-3-Benzyloxy-2-benzyloxymethyl-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetaldehyde → (1S,5R,6R,8R)-6-(4,4'-Dimethoxytrityloxymethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane (191163-55-0)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. NaBH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

2: pyridine / 20 h / Ambient temperature

3: NaH / dimethylformamide / 18 h / 0 °C

4: 82 percent / H₂ / 20percent Pd(OH)2/C / ethanol / 2 h / Ambient temperature

5: 97 percent / pyridine / 5 h / Ambient temperature

With pyridine; sodium tetrahydroborate; hydrogen; sodium hydride; palladium dihydroxide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

upstream raw materials:

4,4'-dimethoxytrityl chloride

(1S,5R,6R,8R)-5-Hydroxy-6-hydroxymethyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose

1,2-O-isopropylidene-3-C-(prop-1-en-3-yl)-α-D-ribofuranose