tert-butyl(((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)methoxy)diphenylsilane

Base Information

• Chemical Name: tert-butyl(((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)methoxy)diphenylsilane
• CAS No.: 1449374-98-4
• Molecular Formula: C₃₉H₅₂O₈Si
• Molecular Weight: 676.923

Synonyms:tert-butyl(((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)methoxy)diphenylsilane

Chemical Property of tert-butyl(((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)methoxy)diphenylsilane

Chemical Property:

Purity/Quality:

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Technology Process of tert-butyl(((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)methoxy)diphenylsilane

There total 13 articles about tert-butyl(((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)methoxy)diphenylsilane 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: 98.0%

(1R,2S)-1-((3aS,4R,6S,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl)-3-((4-methoxybenzyl)oxy)propane-1,2-diol (1449374-96-2) + 2,2-dimethoxy-propane (77-76-9) → tert-butyl(((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)methoxy)diphenylsilane (1449374-98-4)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 0 - 20 ℃; for 4h;

DOI:10.1016/j.tet.2013.05.067

Reference yield:

(2R,3S,4R,5S,6R)-2-(2-methylprop-1-en-1-yl)-6-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol (1449374-89-3) → tert-butyl(((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)methoxy)diphenylsilane (1449374-98-4)

Guidance literature:

Multi-step reaction with 9 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

3.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 2.5 h / 60 °C / Reflux

4.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tert-butyl alcohol / 20 °C / pH 7

4.2: 3407 / 4 h / 20 °C / pH 7

5.1: dichloromethane / 1 h / 20 °C

6.1: diisobutylaluminium hydride / toluene; hexane / -78 - 0 °C

7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 0 - 20 °C

8.1: AD-mix-β; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium osmate(VI) dihydrate; methanesulfonamide / tert-butyl alcohol / pH 7

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

With 1H-imidazole; potassium osmate(VI) dihydrate; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); methanesulfonamide; AD-mix-β; potassium tert-butylate; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; hexane; dichloromethane; acetone; toluene; mineral oil; tert-butyl alcohol; benzene; 3.1: |Barton-McCombie Deoxygenation / 8.1: |Sharpless Dihydroxylation;

DOI:10.1016/j.tet.2013.05.067

Reference yield:

per-O-acetyl-α-D-mannopyranose (4163-65-9) → tert-butyl(((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)methoxy)diphenylsilane (1449374-98-4)

Guidance literature:

Multi-step reaction with 13 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

7.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 2.5 h / 60 °C / Reflux

8.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tert-butyl alcohol / 20 °C / pH 7

8.2: 3407 / 4 h / 20 °C / pH 7

9.1: dichloromethane / 1 h / 20 °C

10.1: diisobutylaluminium hydride / toluene; hexane / -78 - 0 °C

11.1: potassium tert-butylate / tetrahydrofuran / 3 h / 0 - 20 °C

12.1: AD-mix-β; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium osmate(VI) dihydrate; methanesulfonamide / tert-butyl alcohol / pH 7

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

With 1H-imidazole; methanol; iron(III) chloride; potassium osmate(VI) dihydrate; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; methanesulfonamide; AD-mix-β; potassium tert-butylate; hydrogen bromide; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone; toluene; mineral oil; tert-butyl alcohol; benzene; 7.1: |Barton-McCombie Deoxygenation / 12.1: |Sharpless Dihydroxylation;

DOI:10.1016/j.tet.2013.05.067

upstream raw materials:

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

per-O-acetyl-α-D-mannopyranose

acetobromomannose

(2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(2-methylprop-1-en-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

C₂₃H₃₂O₈

(R)-1-((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)ethane-1,2-diol

C₂₄H₃₄O₈

C₃₀H₄₈O₈Si

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