[(3R,4S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,7-dimethyl-2,6,8-tr ioxabicyclo[3.3.0]oct-4-yl]oxy-phenoxy-methanethione

Base Information

• Chemical Name: [(3R,4S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,7-dimethyl-2,6,8-tr ioxabicyclo[3.3.0]oct-4-yl]oxy-phenoxy-methanethione
• CAS No.: 19189-62-9
• Molecular Formula: C19H24 O7 S
• Molecular Weight: 396.461
• Mol file: 19189-62-9.mol

Synonyms:Glucofuranose,1,2:5,6-di-O-isopropylidene-, O-phenyl thiocarbonate, a-D- (8CI); a-D-Glucofuranose,1,2:5,6-bis-O-(1-methylethylidene)-, O-phenyl carbonothioate (9CI); Carbonicacid, thio-, O-phenyl ester, O-ester with 1,2:5,6-di-O-isopropylidene-a-D-glucopyranose (8CI);Furo[2,3-d]-1,3-dioxole, a-D-glucofuranose deriv.

Chemical Property of [(3R,4S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,7-dimethyl-2,6,8-tr ioxabicyclo[3.3.0]oct-4-yl]oxy-phenoxy-methanethione

Chemical Property:

• Vapor Pressure: 4.89E-08mmHg at 25°C
• Boiling Point: 455.1°Cat760mmHg
• Flash Point: 229°C
• PSA: 96.70000
• Density: 1.32g/cm³
• LogP: 2.76340

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [(3R,4S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,7-dimethyl-2,6,8-tr ioxabicyclo[3.3.0]oct-4-yl]oxy-phenoxy-methanethione

There total 8 articles about [(3R,4S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,7-dimethyl-2,6,8-tr ioxabicyclo[3.3.0]oct-4-yl]oxy-phenoxy-methanethione 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: 94.0%

phenylcarbonochloridothioate (1005-56-7) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → O-((3aR,6S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl) O-phenylcarbonothioate (19189-62-9)

Guidance literature:

With pyridine; at 0 - 20 ℃;

DOI:10.1021/acs.orglett.6b02419

Reference yield: 88.0%

phenylcarbonochloridothioate (1005-56-7) + 1,2:5,6-di-O-isopropylidene-α-L-glucofuranose (582-52-5,2595-05-3,10368-86-2,13100-30-6,14686-89-6,23262-79-5,26597-74-0,26623-15-4,38166-58-4,38166-60-8,79943-22-9,83730-28-3) → Thiocarbonic acid O-[(3aS,5S,6R,6aS)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester O-phenyl ester (19189-62-9,145345-66-0)

Guidance literature:

With dmap; In acetonitrile; 0 deg C -> rt;

DOI:10.1021/jo00189a046

Reference yield: 86.0%

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (350255-13-9) + phenylcarbonochloridothioate (1005-56-7) → 1,2:5,6-di-O-isopropylidene-3-O-phenoxythiocarbonyl-α-D-glucofuranose (19189-62-9)

Guidance literature:

With dmap; In acetonitrile; for 16h; Ambient temperature;

DOI:10.1021/ja00350a052

upstream raw materials:

phenylcarbonochloridothioate

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

phenol

D-glucose

Downstream raw materials:

C₁₀H₁₄O₃

1-benzyl-5-hydroxymethyl-hexahydro-cyclopenta[c]isoxazol-6-ol

1-benzyl-5-hydroxymethyl-hexahydro-cyclopenta[c]isoxazol-6-ol

3-benzyl-octahydro-2,4-dioxa-3-aza-cyclopenta[a]pentalene-5,6-diol