(1S,2R,3R,4R)-1-(4-(benzyloxy)phenyl)-4-(benzyloxycarbonylamino)pentane-1,2,3,5-tetrayl tetraacetate

Base Information

• Chemical Name: (1S,2R,3R,4R)-1-(4-(benzyloxy)phenyl)-4-(benzyloxycarbonylamino)pentane-1,2,3,5-tetrayl tetraacetate
• CAS No.: 1346680-25-8
• Molecular Formula: C₃₄H₃₇NO₁₁
• Molecular Weight: 635.668

Synonyms:(1S,2R,3R,4R)-1-(4-(benzyloxy)phenyl)-4-(benzyloxycarbonylamino)pentane-1,2,3,5-tetrayl tetraacetate

Chemical Property of (1S,2R,3R,4R)-1-(4-(benzyloxy)phenyl)-4-(benzyloxycarbonylamino)pentane-1,2,3,5-tetrayl tetraacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3R,4R)-1-(4-(benzyloxy)phenyl)-4-(benzyloxycarbonylamino)pentane-1,2,3,5-tetrayl tetraacetate

There total 16 articles about (1S,2R,3R,4R)-1-(4-(benzyloxy)phenyl)-4-(benzyloxycarbonylamino)pentane-1,2,3,5-tetrayl tetraacetate 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:

C26H29NO7 + acetic anhydride (108-24-7) → (1S,2R,3R,4R)-1-(4-(benzyloxy)phenyl)-4-(benzyloxycarbonylamino)pentane-1,2,3,5-tetrayl tetraacetate (1346680-25-8)

Guidance literature:

With dmap; In dichloromethane; at 0 - 20 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.09.043

Reference yield:

p-benzyloxybenzaldehyde (4397-53-9) → (1S,2R,3R,4R)-1-(4-(benzyloxy)phenyl)-4-(benzyloxycarbonylamino)pentane-1,2,3,5-tetrayl tetraacetate (1346680-25-8)

Guidance literature:

Multi-step reaction with 14 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

13.1: water; acetic acid / 8 h / 20 °C / Inert atmosphere

14.1: dmap / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

With dmap; 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; acetic 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:

(4R,5S)-ethyl 5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate (1346679-74-0) → (1S,2R,3R,4R)-1-(4-(benzyloxy)phenyl)-4-(benzyloxycarbonylamino)pentane-1,2,3,5-tetrayl tetraacetate (1346680-25-8)

Guidance literature:

Multi-step reaction with 11 steps

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

1.2: 2 h / 0 - 20 °C / Inert atmosphere

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

2.2: -78 - 0 °C / Inert atmosphere

3.1: toluene / 6 h / Inert atmosphere; Reflux

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

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

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

6.2: 20 °C / Inert atmosphere; Cooling with ice

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

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

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

10.1: water; acetic acid / 8 h / 20 °C / Inert atmosphere

11.1: dmap / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; thionyl chloride; sodium azide; oxalyl dichloride; ethanol; water; sodium carbonate; potassium carbonate; acetic 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; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Wittig reaction;

DOI:10.1016/j.tetlet.2011.09.043

upstream raw materials:

p-benzyloxybenzaldehyde

(4R,5S)-ethyl 5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

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

(E)-ethyl 3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

Downstream raw materials:

(2R,3R,4R,5R)-4-(hydroxy)-2-(hydroxymethyl)-5-(4-hydroxyphenyl)pyrrolidin-3-ol

(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-(benzyloxy)phenyl)-1-(benzyl-oxycarbonyl)pyrrolidine-3,4-diyl diacetate

(5R,6R,7R,7αR)-5-(4-(benzyloxy)phenyl)-6,7-dihydroxytetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

(5R,6R,7R,7aR)-6,7-dihydroxy-5-(4-hydroxyphenyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

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