ethyl (2R,3R,4S,5R)-2-[N-(benzyloxycarbonyl)amino]-4,5-isopropylidenedioxy-3-methoxyhexanoate

Base Information

• Chemical Name: ethyl (2R,3R,4S,5R)-2-[N-(benzyloxycarbonyl)amino]-4,5-isopropylidenedioxy-3-methoxyhexanoate
• CAS No.: 182216-96-2
• Molecular Formula: C₂₀H₂₉NO₇
• Molecular Weight: 395.453
• Mol file: 182216-96-2.mol

Synonyms:ethyl (2R,3R,4S,5R)-2-[N-(benzyloxycarbonyl)amino]-4,5-isopropylidenedioxy-3-methoxyhexanoate

Chemical Property of ethyl (2R,3R,4S,5R)-2-[N-(benzyloxycarbonyl)amino]-4,5-isopropylidenedioxy-3-methoxyhexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2R,3R,4S,5R)-2-[N-(benzyloxycarbonyl)amino]-4,5-isopropylidenedioxy-3-methoxyhexanoate

There total 4 articles about ethyl (2R,3R,4S,5R)-2-[N-(benzyloxycarbonyl)amino]-4,5-isopropylidenedioxy-3-methoxyhexanoate 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: 99.0%

benzyl chloroformate (501-53-1,94274-21-2) + ethyl (2R,3R,4S,5R)-2-amino-4,5-isopropylidenedioxy-3-methoxyhexanoate (182216-95-1) → ethyl (2R,3R,4S,5R)-2-[N-(benzyloxycarbonyl)amino]-4,5-isopropylidenedioxy-3-methoxyhexanoate (182216-96-2)

Guidance literature:

With sodium hydrogencarbonate; sodium carbonate; In 1,4-dioxane; water; for 2h; Ambient temperature;

DOI:10.1016/0040-4039(96)01173-2

Reference yield:

(3R,6S,1'R,2'S,3'R)-2,5-diethoxy-3,6-dihydro-3-(2,3-isopropylidenedioxy-1-methoxybutyl)-6-isopropylpyrazine (182216-94-0) → ethyl (2R,3R,4S,5R)-2-[N-(benzyloxycarbonyl)amino]-4,5-isopropylidenedioxy-3-methoxyhexanoate (182216-96-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / 0.25N HCl / 5 h / 20 °C

2: 99 percent / Na₂CO₃; NaHCO₃ / dioxane; H₂O / 1 h / 20 °C

With hydrogenchloride; sodium hydrogencarbonate; sodium carbonate; In 1,4-dioxane; water;

DOI:10.1016/S0957-4166(02)00376-2

Reference yield:

(R)-((2R,5S)-3,6-Diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-yl)-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methanol (182216-93-9) → ethyl (2R,3R,4S,5R)-2-[N-(benzyloxycarbonyl)amino]-4,5-isopropylidenedioxy-3-methoxyhexanoate (182216-96-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 0.5 h / 0 °C

1.2: 95 percent / tetrahydrofuran / 12 h / 20 °C

2.1: 80 percent / 0.25N HCl / 5 h / 20 °C

3.1: 99 percent / Na₂CO₃; NaHCO₃ / dioxane; H₂O / 1 h / 20 °C

With hydrogenchloride; sodium hydrogencarbonate; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1016/S0957-4166(02)00376-2

upstream raw materials:

benzyl chloroformate

ethyl (2R,3R,4S,5R)-2-amino-4,5-isopropylidenedioxy-3-methoxyhexanoate

(4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde

(3R,6S,1'R,2'S,3'R)-2,5-diethoxy-3,6-dihydro-3-(2,3-isopropylidenedioxy-1-methoxybutyl)-6-isopropylpyrazine

Downstream raw materials:

(3R,4R,5S,1'R)-3-[N-(benzyloxycarbonyl)amino]-5-[1-(isopropyldimethylsilanyloxy)ethyl]-4-methoxytetrahydrofuran-2-one

(3R,4R,5S,1'R)-3-[N-(benzyloxycarbonyl)amino]-5-(1-hydroxyethyl)-4-methoxytetrahydrofuran-2-one