Dithiocarbonic acid O-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl] ester S-methyl ester

Base Information

• Chemical Name: Dithiocarbonic acid O-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl] ester S-methyl ester
• CAS No.: 847237-60-9
• Molecular Formula: C₆₂H₆₄O₁₁S₂
• Molecular Weight: 1049.32

Synonyms:Dithiocarbonic acid O-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl] ester S-methyl ester

Chemical Property of Dithiocarbonic acid O-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl] ester S-methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Dithiocarbonic acid O-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl] ester S-methyl ester

There total 6 articles about Dithiocarbonic acid O-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenoxy-tetrahydro-pyran-3-yloxy)-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: 90.0%

carbon disulfide (75-15-0,12122-00-8) + methyl iodide (74-88-4) + phenyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside (847237-59-6) → Dithiocarbonic acid O-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl] ester S-methyl ester (847237-60-9)

Guidance literature:

carbon disulfide; phenyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside; With 1H-imidazole; sodium hydride; In tetrahydrofuran;

methyl iodide; In tetrahydrofuran; for 2h;

DOI:10.1016/j.carres.2004.11.017

Reference yield:

(-)-(4,6-O-benzylidene)phenyl-β-D-glucopyranoside (54502-82-8) → Dithiocarbonic acid O-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl] ester S-methyl ester (847237-60-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1.28 g / NaH / dimethylformamide / 20 °C

2.1: 465 mg / sodium cyanoborohydride; HCl / tetrahydrofuran; diethyl ether

3.1: 497 mg / molecular sieves 4 Angstroem; DMTST / CH₂Cl₂; diethyl ether; toluene / 20 °C

4.1: 98 percent / NaOMe / methanol / 20 °C

5.1: NaH; imidazole / tetrahydrofuran

5.2: 90 percent / tetrahydrofuran / 2 h

With 1H-imidazole; hydrogenchloride; 4 A molecular sieve; sodium methylate; sodium hydride; sodium cyanoborohydride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.carres.2004.11.017

Reference yield:

benzyl bromide (100-39-0) → Dithiocarbonic acid O-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl] ester S-methyl ester (847237-60-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1.28 g / NaH / dimethylformamide / 20 °C

2.1: 465 mg / sodium cyanoborohydride; HCl / tetrahydrofuran; diethyl ether

3.1: 497 mg / molecular sieves 4 Angstroem; DMTST / CH₂Cl₂; diethyl ether; toluene / 20 °C

4.1: 98 percent / NaOMe / methanol / 20 °C

5.1: NaH; imidazole / tetrahydrofuran

5.2: 90 percent / tetrahydrofuran / 2 h

With 1H-imidazole; hydrogenchloride; 4 A molecular sieve; sodium methylate; sodium hydride; sodium cyanoborohydride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.carres.2004.11.017

upstream raw materials:

carbon disulfide

methyl iodide

phenyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside

(-)-(4,6-O-benzylidene)phenyl-β-D-glucopyranoside

Downstream raw materials:

phenyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside

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