Dithiocarbonic acid O-((2R,3S,4S,6R)-4-benzyloxy-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yl) ester S-methyl ester

Base Information

• Chemical Name: Dithiocarbonic acid O-((2R,3S,4S,6R)-4-benzyloxy-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yl) ester S-methyl ester
• CAS No.: 106444-95-5
• Molecular Formula: C₃₅H₃₆O₅S₂
• Molecular Weight: 600.8
• Mol file: 106444-95-5.mol

Synonyms:

Chemical Property of Dithiocarbonic acid O-((2R,3S,4S,6R)-4-benzyloxy-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yl) ester S-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Dithiocarbonic acid O-((2R,3S,4S,6R)-4-benzyloxy-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yl) ester S-methyl ester

There total 3 articles about Dithiocarbonic acid O-((2R,3S,4S,6R)-4-benzyloxy-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yl) ester S-methyl ester 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:

methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-ribo-hexopyranoside (63592-79-0) → Dithiocarbonic acid O-((2R,3S,4S,6R)-4-benzyloxy-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yl) ester S-methyl ester (106444-95-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 80.5 percent / p-TsOH, MeOH / CHCl₃ / 3 h / Heating

2: 87 percent / Et₃N, N,N-dimethylaminopyridine / CH₂Cl₂ / 15 h / Heating

3: 1) NaH, imidazole / 1) THf, reflux, 3.5 h, 2) THF, reflux, 2 h

With 1H-imidazole; methanol; dmap; sodium hydride; toluene-4-sulfonic acid; triethylamine; In dichloromethane; chloroform;

DOI:10.1139/v86-296

Reference yield:

(2R,3S,4S)-4-Benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-ol (3868-11-9,64951-98-0,106444-93-3,119874-56-5,151130-22-2) → Dithiocarbonic acid O-((2R,3S,4S,6R)-4-benzyloxy-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yl) ester S-methyl ester (106444-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / Et₃N, N,N-dimethylaminopyridine / CH₂Cl₂ / 15 h / Heating

2: 1) NaH, imidazole / 1) THf, reflux, 3.5 h, 2) THF, reflux, 2 h

With 1H-imidazole; dmap; sodium hydride; triethylamine; In dichloromethane;

DOI:10.1139/v86-296

Reference yield:

carbon disulfide (75-15-0,12122-00-8) + methyl 3-O-benzyl-2-deoxy-6-O-triphenylmethyl-D-ribohexopyranoside (82300-39-8,106444-94-4) + methyl iodide (74-88-4) → Dithiocarbonic acid O-((2R,3S,4S,6S)-4-benzyloxy-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yl) ester S-methyl ester (106444-96-6) + Dithiocarbonic acid O-((2R,3S,4S,6R)-4-benzyloxy-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yl) ester S-methyl ester (106444-95-5)

Guidance literature:

With 1H-imidazole; sodium hydride; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, reflux, 3.5 h, 2) THF, reflux, 2 h;

DOI:10.1139/v86-296

upstream raw materials:

carbon disulfide

methyl 3-O-benzyl-2-deoxy-6-O-triphenylmethyl-D-ribohexopyranoside

methyl iodide

methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-ribo-hexopyranoside

Downstream raw materials:

methyl 3-O-benzyl-2,4-dideoxy-D-erythro-hexopyranoside

(4R,6S)-4-Benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran