3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose

Base Information

• Chemical Name: 3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose
• CAS No.: 219854-34-9
• Molecular Formula: C₂₄H₃₀O₈S
• Molecular Weight: 478.563
• Mol file: 219854-34-9.mol

Synonyms:3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose

Chemical Property of 3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose

Chemical Property:

• Boiling Point: 604.3±55.0 °C(Predicted)
• Density: 1.30±0.1 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

3,?5-?Di-?O-?benzyl-?1,?2-?O-?isopropylidene-?4-?C-?methanesulfonyloxyme?thyl-?α-?D-?ribofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 3,?5-?Di-?O-?benzyl-?1,?2-?O-?isopropylidene-?4-?C-?methanesulfonyloxyme?thyl-?α-?D-?ribofuranose is a reactant used in the preparation of abasic locked nucleic acid derivatives for stability analysis. Also used in the synthesis of oligonucleotides which contain novel thymidine moieties.

Technology Process of 3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose

There total 6 articles about 3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose 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%

methanesulfonyl chloride (124-63-0) + ((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (153186-10-8) → 3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose (219854-34-9)

Guidance literature:

With pyridine;

DOI:10.1039/a806817h

Reference yield: 92.0%

3,5-di-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-a-D-ribothranose + methanesulfonyl chloride (124-63-0) → 3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose (219854-34-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h; Solvent; Reagent/catalyst; Inert atmosphere;

Reference yield:

benzyl bromide (100-39-0) → 3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose (219854-34-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dibutyltin oxide / methanol / 1 h / Heating

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

2.1: 92 percent / pyridine

With pyridine; di(n-butyl)tin oxide; In methanol; 1.1: Substitution / 1.2: Etherification / 2.1: mesylation;

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

upstream raw materials:

methanesulfonyl chloride

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

benzyl bromide

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

Downstream raw materials:

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

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

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

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