(1S,2R)-1-((2R,3R,4S)-3-acetamido-6-(benzyloxycarbonyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-3,4-dihydro-2H-pyran-2-yl)-propane-1,2,3-triyl triacetate

Base Information

Chemical Name:(1S,2R)-1-((2R,3R,4S)-3-acetamido-6-(benzyloxycarbonyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-3,4-dihydro-2H-pyran-2-yl)-propane-1,2,3-triyl triacetate
CAS No.:1384751-64-7
Molecular Formula:C₃₅H₄₈N₄O₁₄
Molecular Weight:748.785
Hs Code.:

(1S,2R)-1-((2R,3R,4S)-3-acetamido-6-(benzyloxycarbonyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-3,4-dihydro-2H-pyran-2-yl)-propane-1,2,3-triyl triacetate

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Chemical Property of (1S,2R)-1-((2R,3R,4S)-3-acetamido-6-(benzyloxycarbonyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-3,4-dihydro-2H-pyran-2-yl)-propane-1,2,3-triyl triacetate

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Technology Process of (1S,2R)-1-((2R,3R,4S)-3-acetamido-6-(benzyloxycarbonyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-3,4-dihydro-2H-pyran-2-yl)-propane-1,2,3-triyl triacetate

There total 8 articles about (1S,2R)-1-((2R,3R,4S)-3-acetamido-6-(benzyloxycarbonyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-3,4-dihydro-2H-pyran-2-yl)-propane-1,2,3-triyl triacetate 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: 82.0%

: 1384751-62-5
(1S,2R)-1-((2R,3R,4S)-3-acetamido-4-amino-6-(benzyloxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

: 207857-15-6
1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine

: 1384751-64-7
(1S,2R)-1-((2R,3R,4S)-3-acetamido-6-(benzyloxycarbonyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-3,4-dihydro-2H-pyran-2-yl)-propane-1,2,3-triyl triacetate

Guidance literature:: With triethylamine; In dichloromethane;
DOI:10.1021/jm3009713

Reference yield:

: 113757-75-8
(2S,4S,5R,6R)-benzyl 5-acetamido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-1-carboxylate

: 1384751-64-7
(1S,2R)-1-((2R,3R,4S)-3-acetamido-6-(benzyloxycarbonyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-3,4-dihydro-2H-pyran-2-yl)-propane-1,2,3-triyl triacetate

Guidance literature:: Multi-step reaction with 6 steps

1: dmap / pyridine / 24 h / 20 °C / Cooling with ice

2: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 2.5 h / 20 - 52 °C / Inert atmosphere

3: acetic acid / ethyl acetate / 24 h / 20 °C

4: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 23 h / 0 - 20 °C / Inert atmosphere

5: hydrogen sulfide / pyridine / 16 h / Inert atmosphere

6: triethylamine / dichloromethane

With dmap; trimethylsilyl trifluoromethanesulfonate; diphenyl phosphoryl azide; hydrogen sulfide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In pyridine; dichloromethane; ethyl acetate; benzene;
DOI:10.1021/jm3009713

Reference yield:

: 113757-76-9
(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(benzyloxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

: 1384751-64-7
(1S,2R)-1-((2R,3R,4S)-3-acetamido-6-(benzyloxycarbonyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-3,4-dihydro-2H-pyran-2-yl)-propane-1,2,3-triyl triacetate

Guidance literature:: Multi-step reaction with 5 steps

1: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 2.5 h / 20 - 52 °C / Inert atmosphere

2: acetic acid / ethyl acetate / 24 h / 20 °C

3: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 23 h / 0 - 20 °C / Inert atmosphere

4: hydrogen sulfide / pyridine / 16 h / Inert atmosphere

5: triethylamine / dichloromethane

With trimethylsilyl trifluoromethanesulfonate; diphenyl phosphoryl azide; hydrogen sulfide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In pyridine; dichloromethane; ethyl acetate; benzene;
DOI:10.1021/jm3009713