(3aR,4R,6S,6aS)-6-(bromomethyl)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,4R,6S,6aS)-6-(bromomethyl)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS No.: 38838-05-0
• Molecular Formula: C9H15BrO4
• Molecular Weight: 267.12
• Nikkaji Number: J319.846D
• Mol file: 38838-05-0.mol

Synonyms:SCHEMBL15077387;NS00059482

Chemical Property of (3aR,4R,6S,6aS)-6-(bromomethyl)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole

Chemical Property:

• Boiling Point: 295.4°Cat760mmHg
• Flash Point: 118.4°C
• PSA: 57.15000
• Density: 1.47g/cm³
• LogP: 0.59110
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 266.01537
• Heavy Atom Count: 14
• Complexity: 221

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(OC(C2O1)OC)CBr)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H](O[C@H]([C@@H]2O1)OC)CBr)C

Technology Process of (3aR,4R,6S,6aS)-6-(bromomethyl)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole

There total 17 articles about (3aR,4R,6S,6aS)-6-(bromomethyl)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole 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: 97.0%

1-O-methyl-2,3-O-isopropylidene-5-O-(methanesulfonyl)-β-D-ribofuranoside (50610-99-6,75100-24-2,81026-76-8,96896-28-5) → 1-O-methyl-2,3-O-isopropylidene-5-bromo-5-deoxy-β-D-ribofuranoside (38838-05-0)

Guidance literature:

With lithium bromide; In N,N-dimethyl-formamide; for 0.5h; Reflux;

DOI:10.1016/j.molliq.2020.115167

Reference yield: 95.0%

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (4099-85-8,828937-29-7) → 1-O-methyl-2,3-O-isopropylidene-5-bromo-5-deoxy-β-D-ribofuranoside (38838-05-0)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1134/S1070428007050168

Reference yield: 89.0%

methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside (4137-56-8) → 1-O-methyl-2,3-O-isopropylidene-5-bromo-5-deoxy-β-D-ribofuranoside (38838-05-0)

Guidance literature:

With tetrabutylammomium bromide; In N,N-dimethyl-formamide; for 24h; Heating;

DOI:10.1071/CH01036

upstream raw materials:

(methyl 5-deoxy-2,3-O-isopropylidene-methyl-β-D-ribo-hexafuranoside)uronic acid

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

2-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-1,3-diphenyl-[1,3,2]diazaphospholidine

Pyridine-2-sulfonic acid (3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester

Downstream raw materials:

methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside

(R)-2,3-dibenzyloxypropyl 5-bromo-5-deoxy-2,3-O-isopropylidene-β-D-riboside

1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose

5-O-deoxy-D-ribofuranose