(1R,6R,7R,9R)-7-(4,4'-Dimethoxytrityloxymethyl)-6-hydroxy-9-(thymin-1-yl)-2,8-dioxabicyclo[4.3.0]nonane

Base Information

• Chemical Name: (1R,6R,7R,9R)-7-(4,4'-Dimethoxytrityloxymethyl)-6-hydroxy-9-(thymin-1-yl)-2,8-dioxabicyclo[4.3.0]nonane
• CAS No.: 201358-18-1
• Molecular Formula: C₃₄H₃₆N₂O₈
• Molecular Weight: 600.668
• Mol file: 201358-18-1.mol

Synonyms:(1R,6R,7R,9R)-7-(4,4'-Dimethoxytrityloxymethyl)-6-hydroxy-9-(thymin-1-yl)-2,8-dioxabicyclo[4.3.0]nonane

Chemical Property of (1R,6R,7R,9R)-7-(4,4'-Dimethoxytrityloxymethyl)-6-hydroxy-9-(thymin-1-yl)-2,8-dioxabicyclo[4.3.0]nonane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,6R,7R,9R)-7-(4,4'-Dimethoxytrityloxymethyl)-6-hydroxy-9-(thymin-1-yl)-2,8-dioxabicyclo[4.3.0]nonane

There total 17 articles about (1R,6R,7R,9R)-7-(4,4'-Dimethoxytrityloxymethyl)-6-hydroxy-9-(thymin-1-yl)-2,8-dioxabicyclo[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: 99.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + (1R,6R,7R,9R)-6-Hydroxy-7-hydroxymethyl-9-(thymin-1-yl)-2,8-dioxabicyclo[4.3.0]nonane (201358-12-5) → (1R,6R,7R,9R)-7-(4,4'-Dimethoxytrityloxymethyl)-6-hydroxy-9-(thymin-1-yl)-2,8-dioxabicyclo[4.3.0]nonane (201358-18-1)

Guidance literature:

With pyridine; for 5h; Ambient temperature;

Reference yield:

1,2-O-isopropylidene-3-C-(prop-1-en-3-yl)-α-D-ribofuranose (151426-67-4) → (1R,6R,7R,9R)-7-(4,4'-Dimethoxytrityloxymethyl)-6-hydroxy-9-(thymin-1-yl)-2,8-dioxabicyclo[4.3.0]nonane (201358-18-1)

Guidance literature:

Multi-step reaction with 8 steps

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

2: 82 percent / aq. HCl / 18 h / Ambient temperature

3: 1.) BH₃*1,4-oxathiane, 2.) H₂O₂ / 1.) THF, r.t., 45 min, 2.) aq. NaOH, r.t., 1 h

4: pyridine / 1.5 h / 0 °C

5: KOH, 18-crown-6 / dimethylformamide / 4 h / Ambient temperature

6: 19 percent / BSA, TMS triflate / dimethylformamide / 1.) reflux, 15 min, 2.) r.t., 18 h; 50 deg C, 4 h

7: 73 percent / H₂ / 20percent Pd(OH)2/C / ethanol / 2 h / Ambient temperature

8: 99 percent / pyridine / 5 h / Ambient temperature

With pyridine; hydrogenchloride; benzenesulfonamide; potassium hydroxide; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; borane:1,4-oxathiane; hydrogen; dihydrogen peroxide; sodium hydride; palladium dihydroxide; In ethanol; N,N-dimethyl-formamide;

Reference yield:

5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose (103931-45-9) → (1R,6R,7R,9R)-7-(4,4'-Dimethoxytrityloxymethyl)-6-hydroxy-9-(thymin-1-yl)-2,8-dioxabicyclo[4.3.0]nonane (201358-18-1)

Guidance literature:

Multi-step reaction with 10 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: 82 percent / aq. HCl / 18 h / Ambient temperature

5: 1.) BH₃*1,4-oxathiane, 2.) H₂O₂ / 1.) THF, r.t., 45 min, 2.) aq. NaOH, r.t., 1 h

6: pyridine / 1.5 h / 0 °C

7: KOH, 18-crown-6 / dimethylformamide / 4 h / Ambient temperature

8: 19 percent / BSA, TMS triflate / dimethylformamide / 1.) reflux, 15 min, 2.) r.t., 18 h; 50 deg C, 4 h

9: 73 percent / H₂ / 20percent Pd(OH)2/C / ethanol / 2 h / Ambient temperature

10: 99 percent / pyridine / 5 h / Ambient temperature

With pyridine; hydrogenchloride; benzenesulfonamide; potassium hydroxide; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; borane:1,4-oxathiane; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hydride; palladium dihydroxide; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide;

upstream raw materials:

4,4'-dimethoxytrityl chloride

(1R,6R,7R,9R)-6-Hydroxy-7-hydroxymethyl-9-(thymin-1-yl)-2,8-dioxabicyclo[4.3.0]nonane

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