O-((3aR,4R,6R,7R,7aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methylprop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl)-S-methyl carbonodithioate

Base Information

Chemical Name:O-((3aR,4R,6R,7R,7aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methylprop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl)-S-methyl carbonodithioate
CAS No.:1449374-91-7
Molecular Formula:C₃₁H₄₂O₅S₂Si
Molecular Weight:586.889
Hs Code.:

O-((3aR,4R,6R,7R,7aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methylprop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl)-S-methyl carbonodithioate

Synonyms:O-((3aR,4R,6R,7R,7aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methylprop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl)-S-methyl carbonodithioate

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Chemical Property of O-((3aR,4R,6R,7R,7aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methylprop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl)-S-methyl carbonodithioate

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Technology Process of O-((3aR,4R,6R,7R,7aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methylprop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl)-S-methyl carbonodithioate

There total 6 articles about O-((3aR,4R,6R,7R,7aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methylprop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl)-S-methyl carbonodithioate 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%

: 75-15-0,12122-00-8
carbon disulfide

: 1449374-90-6
(3aR,4R,6R,7R,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methyl-prop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol

: 74-88-4
methyl iodide

: 1449374-91-7
O-((3aR,4R,6R,7R,7aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methylprop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl)-S-methyl carbonodithioate

Guidance literature:: (3aR,4R,6R,7R,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methyl-prop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol; With 1H-imidazole; sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃;

carbon disulfide; In tetrahydrofuran; mineral oil; at 20 ℃; for 0.5h;

methyl iodide; In tetrahydrofuran; mineral oil; for 0.166667h;
DOI:10.1016/j.tet.2013.05.067

Reference yield:

: 1449374-89-3
(2R,3S,4R,5S,6R)-2-(2-methylprop-1-en-1-yl)-6-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

: 1449374-91-7
O-((3aR,4R,6R,7R,7aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methylprop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl)-S-methyl carbonodithioate

Guidance literature:: Multi-step reaction with 2 steps

1.1: toluene-4-sulfonic acid / acetone / 4 h / 0 - 20 °C

2.1: 1H-imidazole; sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C

2.2: 0.5 h / 20 °C

2.3: 0.17 h

With 1H-imidazole; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; acetone; mineral oil;
DOI:10.1016/j.tet.2013.05.067

Reference yield:

: 4163-65-9
per-O-acetyl-α-D-mannopyranose

: 1449374-91-7
O-((3aR,4R,6R,7R,7aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methylprop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl)-S-methyl carbonodithioate

Guidance literature:: Multi-step reaction with 6 steps

1.1: hydrogen bromide / dichloromethane; acetic acid / 0 - 20 °C

2.1: iron(III) chloride; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 20 °C

3.1: potassium carbonate; methanol / 20 °C

4.1: 1H-imidazole / N,N-dimethyl-formamide / 5 h / 0 - 20 °C

5.1: toluene-4-sulfonic acid / acetone / 4 h / 0 - 20 °C

6.1: 1H-imidazole; sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C

6.2: 0.5 h / 20 °C

6.3: 0.17 h

With 1H-imidazole; methanol; iron(III) chloride; N,N,N,N,-tetramethylethylenediamine; hydrogen bromide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone; mineral oil;
DOI:10.1016/j.tet.2013.05.067