1-{2-O-acetyl-3-O-benzyl-4-[(benzyloxy)methyl]-5-O-(methylsulfonyl)-α-L-lyxofuranosyl}-5-methylpyrimidine-2,4-(1H,3H)-dione

Base Information

• Chemical Name: 1-{2-O-acetyl-3-O-benzyl-4-[(benzyloxy)methyl]-5-O-(methylsulfonyl)-α-L-lyxofuranosyl}-5-methylpyrimidine-2,4-(1H,3H)-dione
• CAS No.: 263547-06-4
• Molecular Formula: C₂₈H₃₂N₂O₁₀S
• Molecular Weight: 588.635
• Mol file: 263547-06-4.mol

Synonyms:1-{2-O-acetyl-3-O-benzyl-4-[(benzyloxy)methyl]-5-O-(methylsulfonyl)-α-L-lyxofuranosyl}-5-methylpyrimidine-2,4-(1H,3H)-dione

Chemical Property of 1-{2-O-acetyl-3-O-benzyl-4-[(benzyloxy)methyl]-5-O-(methylsulfonyl)-α-L-lyxofuranosyl}-5-methylpyrimidine-2,4-(1H,3H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{2-O-acetyl-3-O-benzyl-4-[(benzyloxy)methyl]-5-O-(methylsulfonyl)-α-L-lyxofuranosyl}-5-methylpyrimidine-2,4-(1H,3H)-dione

There total 7 articles about 1-{2-O-acetyl-3-O-benzyl-4-[(benzyloxy)methyl]-5-O-(methylsulfonyl)-α-L-lyxofuranosyl}-5-methylpyrimidine-2,4-(1H,3H)-dione 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: 86.0%

thymin (65-71-4,28806-14-6,691841-57-3) + 1,2-di-O-acetyl-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-O-(methylsulfonyl)-L-lyxofuranose (221229-65-8) → 1-{2-O-acetyl-3-O-benzyl-4-[(benzyloxy)methyl]-5-O-(methylsulfonyl)-α-L-lyxofuranosyl}-5-methylpyrimidine-2,4-(1H,3H)-dione (263547-06-4)

Guidance literature:

thymin; 1,2-di-O-acetyl-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-O-(methylsulfonyl)-L-lyxofuranose; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 0 - 50 ℃; for 3h; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 - 50 ℃;

Reference yield:

3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose (219854-34-9) → 1-{2-O-acetyl-3-O-benzyl-4-[(benzyloxy)methyl]-5-O-(methylsulfonyl)-α-L-lyxofuranosyl}-5-methylpyrimidine-2,4-(1H,3H)-dione (263547-06-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: AcOH; H₂O / 3 h / 90 °C

1.2: 54 percent / pyridine / 12 h / 20 °C

2.1: 75 percent / N,O-bis(trimethylsiyl)acetamide; Me₃SiOTf / acetonitrile

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; water; acetic acid; In acetonitrile; 1.1: Hydrolysis / 1.2: Acetylation / 2.1: Substitution;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<128::AID-HLCA128>3.0.CO;2-Q

Reference yield:

benzyl bromide (100-39-0) → 1-{2-O-acetyl-3-O-benzyl-4-[(benzyloxy)methyl]-5-O-(methylsulfonyl)-α-L-lyxofuranosyl}-5-methylpyrimidine-2,4-(1H,3H)-dione (263547-06-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dibutyltin oxide / methanol / 1 h / Heating

1.2: 19 percent / Bu₄NBr / toluene / 15 h / Heating

2.1: 92 percent / pyridine

3.1: AcOH; H₂O / 3 h / 90 °C

3.2: 54 percent / pyridine / 12 h / 20 °C

4.1: 75 percent / N,O-bis(trimethylsiyl)acetamide; Me₃SiOTf / acetonitrile

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; water; di(n-butyl)tin oxide; acetic acid; In methanol; acetonitrile; 1.1: Substitution / 1.2: Etherification / 2.1: mesylation / 3.1: Hydrolysis / 3.2: Acetylation / 4.1: Substitution;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<128::AID-HLCA128>3.0.CO;2-Q

upstream raw materials:

thymin

1,2-di-O-acetyl-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-O-(methylsulfonyl)-L-lyxofuranose

benzyl bromide

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Downstream raw materials:

(1S,3R,4R,7S)-7-(benzyloxy)-1-[(benzyloxy)methyl]-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane