(1S,3R,9R,10R,12R)-3-(3(S)-hydroxy-5(R)-(thymin-1-yl)tetrahydrofuran-2(R)-yl)methoxy-3-oxo-12-(4,4'-dimethoxytrityl)oxymethyl-10-(thymin-1-yl)-2,4,11-trioxa-3-phosphabicyclo[7.3.0]dodecan

Base Information

• Chemical Name: (1S,3R,9R,10R,12R)-3-(3(S)-hydroxy-5(R)-(thymin-1-yl)tetrahydrofuran-2(R)-yl)methoxy-3-oxo-12-(4,4'-dimethoxytrityl)oxymethyl-10-(thymin-1-yl)-2,4,11-trioxa-3-phosphabicyclo[7.3.0]dodecan
• CAS No.: 860026-88-6
• Molecular Formula: C₄₄H₄₉N₄O₁₄P
• Molecular Weight: 888.865
• Mol file: 860026-88-6.mol

Synonyms:(1S,3R,9R,10R,12R)-3-(3(S)-hydroxy-5(R)-(thymin-1-yl)tetrahydrofuran-2(R)-yl)methoxy-3-oxo-12-(4,4'-dimethoxytrityl)oxymethyl-10-(thymin-1-yl)-2,4,11-trioxa-3-phosphabicyclo[7.3.0]dodecan

Chemical Property of (1S,3R,9R,10R,12R)-3-(3(S)-hydroxy-5(R)-(thymin-1-yl)tetrahydrofuran-2(R)-yl)methoxy-3-oxo-12-(4,4'-dimethoxytrityl)oxymethyl-10-(thymin-1-yl)-2,4,11-trioxa-3-phosphabicyclo[7.3.0]dodecan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,9R,10R,12R)-3-(3(S)-hydroxy-5(R)-(thymin-1-yl)tetrahydrofuran-2(R)-yl)methoxy-3-oxo-12-(4,4'-dimethoxytrityl)oxymethyl-10-(thymin-1-yl)-2,4,11-trioxa-3-phosphabicyclo[7.3.0]dodecan

There total 3 articles about (1S,3R,9R,10R,12R)-3-(3(S)-hydroxy-5(R)-(thymin-1-yl)tetrahydrofuran-2(R)-yl)methoxy-3-oxo-12-(4,4'-dimethoxytrityl)oxymethyl-10-(thymin-1-yl)-2,4,11-trioxa-3-phosphabicyclo[7.3.0]dodecan 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: 64.0%

(1S,3R,9R,10R,12R)-3-(3(S)-hydroxy-5(R)-(thymin-1-yl)tetrahydrofuran-2(R)-yl)methoxy-3-oxo-12-hydroxymethyl-10-(thymin-1-yl)-2,4,11-trioxa-3-phosphabicyclo[7.3.0]dodecan (860026-86-4) + 4,4'-dimethoxytrityl chloride (40615-36-9) → (1S,3R,9R,10R,12R)-3-(3(S)-hydroxy-5(R)-(thymin-1-yl)tetrahydrofuran-2(R)-yl)methoxy-3-oxo-12-(4,4'-dimethoxytrityl)oxymethyl-10-(thymin-1-yl)-2,4,11-trioxa-3-phosphabicyclo[7.3.0]dodecan (860026-88-6)

Guidance literature:

With 2,6-dimethylpyridine; In dimethyl sulfoxide; at 20 ℃; for 48h;

DOI:10.1039/b502720a

Reference yield:

(1S,3RS,9R,10R,12R)-3-(3(S)-(tert-butyldimethylsilyl)oxy-5(R)-(thymin-1-yl)tetrahydrofuran-2(R)-yl)methoxy-3-oxo-12-(tert-butyldimethylsilyl)oxymethyl-10-(thymin-1-yl)-2,4,11-trioxa-3-phosphabicyclo[7.3.0]dodec-6-ene → (1S,3R,9R,10R,12R)-3-(3(S)-hydroxy-5(R)-(thymin-1-yl)tetrahydrofuran-2(R)-yl)methoxy-3-oxo-12-(4,4'-dimethoxytrityl)oxymethyl-10-(thymin-1-yl)-2,4,11-trioxa-3-phosphabicyclo[7.3.0]dodecan (860026-88-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.092 g / H₂ / Grubbs 2nd generation catalyst / CH₂Cl₂ / 12 h / 50 °C / 51714.8 Torr

2: 100 percent / aq. TFA / 4.83 h

3: 64 percent / 2,6-lutidine / dimethylsulfoxide / 48 h / 20 °C

With 2,6-dimethylpyridine; hydrogen; trifluoroacetic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; dimethyl sulfoxide;

DOI:10.1039/b502720a

Reference yield:

(1S,3R,9R,10R,12R)-3-(3(S)-(tert-butyldimethylsilyl)oxy-5(R)-(thymin-1-yl)tetrahydrofuran-2(R)-yl)methoxy-3-oxo-12-(tert-butyldimethylsilyl)oxymethyl-10-(thymin-1-yl)-2,4,11-trioxa-3-phosphabicyclo[7.3.0]dodecane (860026-84-2) → (1S,3R,9R,10R,12R)-3-(3(S)-hydroxy-5(R)-(thymin-1-yl)tetrahydrofuran-2(R)-yl)methoxy-3-oxo-12-(4,4'-dimethoxytrityl)oxymethyl-10-(thymin-1-yl)-2,4,11-trioxa-3-phosphabicyclo[7.3.0]dodecan (860026-88-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / aq. TFA / 4.83 h

2: 64 percent / 2,6-lutidine / dimethylsulfoxide / 48 h / 20 °C

With 2,6-dimethylpyridine; trifluoroacetic acid; In dimethyl sulfoxide;

DOI:10.1039/b502720a

upstream raw materials:

(1S,3R,9R,10R,12R)-3-(3(S)-hydroxy-5(R)-(thymin-1-yl)tetrahydrofuran-2(R)-yl)methoxy-3-oxo-12-hydroxymethyl-10-(thymin-1-yl)-2,4,11-trioxa-3-phosphabicyclo[7.3.0]dodecan

4,4'-dimethoxytrityl chloride

(1S,3R,9R,10R,12R)-3-(3(S)-(tert-butyldimethylsilyl)oxy-5(R)-(thymin-1-yl)tetrahydrofuran-2(R)-yl)methoxy-3-oxo-12-(tert-butyldimethylsilyl)oxymethyl-10-(thymin-1-yl)-2,4,11-trioxa-3-phosphabicyclo[7.3.0]dodecane