3-O-Benzyl 4-C-(methanesulfonyloxymethyl)-5-O-methanesulfonyl-1,2-O-isopropylidene-a-D-ribofuranose

Base Information

• Chemical Name: 3-O-Benzyl 4-C-(methanesulfonyloxymethyl)-5-O-methanesulfonyl-1,2-O-isopropylidene-a-D-ribofuranose
• CAS No.: 293751-01-6
• Molecular Formula: C18H26O10S2
• Molecular Weight: 466.53
• European Community (EC) Number: 805-403-2
• DSSTox Substance ID: DTXSID20432102
• Wikidata: Q72490630
• Mol file: 293751-01-6.mol

Synonyms:293751-01-6;3-O-Benzyl 4-C-(methanesulfonyloxymethyl)-5-O-methanesulfonyl-1,2-O-isopropylidene-a-D-ribofuranose;[(3aR,6S,6aR)-2,2-dimethyl-5-(methylsulfonyloxymethyl)-6-phenylmethoxy-6,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]methyl methanesulfonate;((3aR,6S,6aR)-6-(Benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5,5-diyl)bis(methylene) dimethanesulfonate;DTXSID20432102;W-202223;((3aR,6S,6aR)-6-(Benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5,5-diyl)bis(methylene)dimethanesulfonate;[(3aR,6S,6aR)-6-(Benzyloxy)-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxole-5,5-diyl]bis(methylene) dimethanesulfonate (non-preferred name)

Chemical Property of 3-O-Benzyl 4-C-(methanesulfonyloxymethyl)-5-O-methanesulfonyl-1,2-O-isopropylidene-a-D-ribofuranose

Chemical Property:

• PSA: 140.42000
• LogP: 2.93240
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 466.09673937
• Heavy Atom Count: 30
• Complexity: 754

Purity/Quality:

99% ^*data from raw suppliers

3-O-Benzyl4-C-(Methanesulfonyloxymethyl)-5-O-methanesulfonyl-1,2-O-isopropylidene-α-D-ribofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(C(OC2O1)(COS(=O)(=O)C)COS(=O)(=O)C)OCC3=CC=CC=C3)C
• Isomeric SMILES: CC1(O[C@@H]2[C@@H](C(O[C@@H]2O1)(COS(=O)(=O)C)COS(=O)(=O)C)OCC3=CC=CC=C3)C

Technology Process of 3-O-Benzyl 4-C-(methanesulfonyloxymethyl)-5-O-methanesulfonyl-1,2-O-isopropylidene-a-D-ribofuranose

There total 10 articles about 3-O-Benzyl 4-C-(methanesulfonyloxymethyl)-5-O-methanesulfonyl-1,2-O-isopropylidene-a-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: 98.0%

methanesulfonyl chloride (124-63-0) + 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 3-O-benzyl-4-C-methanesulfonoxymethyl-5-methanesulfonyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (293751-01-6)

Guidance literature:

With pyridine; at 20 ℃; for 1h;

DOI:10.1021/jo010732p

Reference yield:

Diacetone D-glucose (2595-05-3) → 3-O-benzyl-4-C-methanesulfonoxymethyl-5-methanesulfonyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (293751-01-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / mineral oil; acetonitrile / 1 h / 0 °C / Inert atmosphere

1.2: 4.5 h / 0 °C

2.1: acetic acid / water / 72 h / 20 °C

3.1: sodium periodate / water / 1 h / 0 °C

4.1: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C

5.1: pyridine / 1 h / 20 °C

With pyridine; sodium periodate; sodium hydride; acetic acid; sodium hydroxide; In 1,4-dioxane; water; acetonitrile; mineral oil;

DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose (22331-21-1) → 3-O-benzyl-4-C-methanesulfonoxymethyl-5-methanesulfonyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (293751-01-6)

Guidance literature:

Multi-step reaction with 4 steps

1: acetic acid / water / 72 h / 20 °C

2: sodium periodate / water / 1 h / 0 °C

3: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C

4: pyridine / 1 h / 20 °C

With pyridine; sodium periodate; acetic acid; sodium hydroxide; In 1,4-dioxane; water;

DOI:10.1016/j.bmcl.2014.04.050

upstream raw materials:

methanesulfonyl chloride

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

Diacetone D-glucose

benzyl bromide

Downstream raw materials:

methyl (3-O-benzyl-5-O-methylsulfonyl-4-C-methylsulfonyloxymethyl)-D-ribofuranoside

1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-erythro-pentofuranosyl)thymine

1-(3-O-benzyl-5-O-methylsulfonyl-4-C-methylsulfonyloxymethyl-α-D-ribofuranosyl)thymine

Refernces

• 1、 Sharma, Vivek K.,Kumar, Manish,Olsen, Carl E.,Prasad, Ashok K.. "Chemoenzymatic convergent synthesis of 2'-o,4'-c-methyleneribonucleosides". supporting information. p. 6336 - 6341. Retrieved 2014/07/21.
• 2、 Madsen, Andreas Stahl,Jorgensen, Anna Sondergaard,Jensen, Troels Bundgaard,Wengel, Jesper. "Large scale synthesis of 2′-Amino-LNA thymine and 5-methylcytosine nucleosides". . p. 10718 - 10728. Retrieved 2013/02/23.