benzyl (1R,2R)-1-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-dihydroxypropan-2-ylcarbamate

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Chemical Name:benzyl (1R,2R)-1-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-dihydroxypropan-2-ylcarbamate
CAS No.:1346680-08-7
Molecular Formula:C₂₉H₃₃NO₇
Molecular Weight:507.584
Hs Code.:

Synonyms:benzyl (1R,2R)-1-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-dihydroxypropan-2-ylcarbamate

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Chemical Property of benzyl (1R,2R)-1-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-dihydroxypropan-2-ylcarbamate

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Technology Process of benzyl (1R,2R)-1-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-dihydroxypropan-2-ylcarbamate

There total 14 articles about benzyl (1R,2R)-1-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-dihydroxypropan-2-ylcarbamate 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: 78.0%

: 1346680-03-2
(2S,3R)-ethyl 3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(benzyloxycarbonylamino)-3-hydroxypropanoate

: 1346680-08-7
benzyl (1R,2R)-1-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-dihydroxypropan-2-ylcarbamate

Guidance literature:: With sodium tetrahydroborate; lithium chloride; In tetrahydrofuran; ethanol; at 0 - 20 ℃; for 3.33333h; Inert atmosphere;
DOI:10.1016/j.tetlet.2011.09.043

Reference yield:

: 4397-53-9
p-benzyloxybenzaldehyde

: 1346680-08-7
benzyl (1R,2R)-1-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-dihydroxypropan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 12 steps

1.1: toluene / 4 h / Inert atmosphere; Reflux

2.1: AD-mix-α; methanesulfonamide; water / tert-butyl alcohol / 24 h / 0 °C / Inert atmosphere

3.1: toluene-4-sulfonic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.33 h / 0 - 20 °C / Inert atmosphere

4.2: 2 h / 0 - 20 °C / Inert atmosphere

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.67 h / -78 °C / Inert atmosphere

5.2: -78 - 0 °C / Inert atmosphere

6.1: toluene / 6 h / Inert atmosphere; Reflux

7.1: osmium(VIII) oxide; water; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III) / tert-butyl alcohol / 24.08 h / 0 °C / Inert atmosphere

8.1: thionyl chloride; triethylamine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

9.1: sodium azide / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere

9.2: 20 °C / Inert atmosphere; Cooling with ice

10.1: ethanol; triphenylphosphine / 6 h / 0 - 20 °C / Inert atmosphere

11.1: sodium carbonate / ethanol / 8 h / 0 - 20 °C / Inert atmosphere

12.1: sodium tetrahydroborate; lithium chloride / tetrahydrofuran; ethanol / 3.33 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; thionyl chloride; sodium azide; oxalyl dichloride; ethanol; methanesulfonamide; AD-mix-α; water; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; triphenylphosphine; lithium chloride; potassium hexacyanoferrate(III); In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Wittig reaction / 2.1: Sharpless dihydroxylation / 5.1: Swern oxidation / 5.2: Swern oxidation / 6.1: Wittig reaction;
DOI:10.1016/j.tetlet.2011.09.043

Reference yield:

: 1346679-78-4
((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol

: 1346680-08-7
benzyl (1R,2R)-1-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-dihydroxypropan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 8 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.67 h / -78 °C / Inert atmosphere

1.2: -78 - 0 °C / Inert atmosphere

2.1: toluene / 6 h / Inert atmosphere; Reflux

3.1: osmium(VIII) oxide; water; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III) / tert-butyl alcohol / 24.08 h / 0 °C / Inert atmosphere

4.1: thionyl chloride; triethylamine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

5.1: sodium azide / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere; Cooling with ice

6.1: ethanol; triphenylphosphine / 6 h / 0 - 20 °C / Inert atmosphere

7.1: sodium carbonate / ethanol / 8 h / 0 - 20 °C / Inert atmosphere

8.1: sodium tetrahydroborate; lithium chloride / tetrahydrofuran; ethanol / 3.33 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; osmium(VIII) oxide; thionyl chloride; sodium azide; oxalyl dichloride; ethanol; water; sodium carbonate; potassium carbonate; dimethyl sulfoxide; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; triphenylphosphine; lithium chloride; potassium hexacyanoferrate(III); In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.1: Wittig reaction;
DOI:10.1016/j.tetlet.2011.09.043