1,2-O-isopropylidene-5-O-methylsulphonyl-3-O-(p-methoxybenzyl)-α-D-ribofuranose

Base Information

• Chemical Name: 1,2-O-isopropylidene-5-O-methylsulphonyl-3-O-(p-methoxybenzyl)-α-D-ribofuranose
• CAS No.: 115693-79-3
• Molecular Formula: C₁₇H₂₄O₈S
• Molecular Weight: 388.439
• Mol file: 115693-79-3.mol

Synonyms:1,2-O-isopropylidene-5-O-methylsulphonyl-3-O-(p-methoxybenzyl)-α-D-ribofuranose

Chemical Property of 1,2-O-isopropylidene-5-O-methylsulphonyl-3-O-(p-methoxybenzyl)-α-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-O-isopropylidene-5-O-methylsulphonyl-3-O-(p-methoxybenzyl)-α-D-ribofuranose

There total 7 articles about 1,2-O-isopropylidene-5-O-methylsulphonyl-3-O-(p-methoxybenzyl)-α-D-ribofuranose 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: 96.0%

methanesulfonyl chloride (124-63-0) + 1,2-O-isopropylidene-3-O-(p-methoxybenzyl)-α-D-ribofuranose (109536-52-9) → 1,2-O-isopropylidene-5-O-methylsulphonyl-3-O-(p-methoxybenzyl)-α-D-ribofuranose (115693-79-3)

Guidance literature:

In pyridine; for 2.5h; Ambient temperature;

DOI:10.1039/P19870002681

Reference yield:

(1,2:5,6)-di-O-isopropylidene-D-gulose (14686-89-6) → 1,2-O-isopropylidene-5-O-methylsulphonyl-3-O-(p-methoxybenzyl)-α-D-ribofuranose (115693-79-3)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydride / tetrahydrofuran / 48 h / Heating

2: 0.8percent sulphuric acid / methanol / 72 h / Ambient temperature

3: 1.) sodium periodate; 2.) sodium borohydride; / 1.) water, MeOH, 2 h, r.t.; 2.) 2 h, r.t.

4: 96 percent / pyridine / 2.5 h / Ambient temperature

With sodium tetrahydroborate; sodium periodate; sulfuric acid; sodium hydride; In tetrahydrofuran; pyridine; methanol;

DOI:10.1039/P19870002681

Reference yield:

(R)-1-[(3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol (69940-04-1,142226-16-2,109536-51-8) → 1,2-O-isopropylidene-5-O-methylsulphonyl-3-O-(p-methoxybenzyl)-α-D-ribofuranose (115693-79-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) sodium periodate; 2.) sodium borohydride; / 1.) water, MeOH, 2 h, r.t.; 2.) 2 h, r.t.

2: 96 percent / pyridine / 2.5 h / Ambient temperature

With sodium tetrahydroborate; sodium periodate; In pyridine;

DOI:10.1039/P19870002681

upstream raw materials:

methanesulfonyl chloride

1,2-O-isopropylidene-3-O-(p-methoxybenzyl)-α-D-ribofuranose

(1,2:5,6)-di-O-isopropylidene-D-gulose

(R)-1-[(3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol

Downstream raw materials:

methyl 5-deoxy-3-O-(p-methoxybenzyl)-β-D-ribofuranoside

methyl 5-deoxy-3-O-(p-methoxybenzyl)-α-D-ribofuranoside

(4R,5S)-3-Hexadec-(Z)-ylidene-4-(4-methoxy-benzyloxy)-5-methyl-dihydro-furan-2-one

(4R,5S)-3-Hexadec-(E)-ylidene-4-(4-methoxy-benzyloxy)-5-methyl-dihydro-furan-2-one