(2R,3R,4S,5S)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxypiperidine

Base Information

• Chemical Name: (2R,3R,4S,5S)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxypiperidine
• CAS No.: 1429413-06-8
• Molecular Formula: C₂₉H₄₅NO₄Si
• Molecular Weight: 499.766
• Mol file: 1429413-06-8.mol

Synonyms:(2R,3R,4S,5S)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxypiperidine

Chemical Property of (2R,3R,4S,5S)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxypiperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5S)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxypiperidine

There total 10 articles about (2R,3R,4S,5S)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxypiperidine 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: 100.0%

(2R,3R,4S,5S)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-diacetoxypiperidine (1429413-08-0) → (2R,3R,4S,5S)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxypiperidine (1429413-06-8)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 16h;

DOI:10.1021/ol400735z

Reference yield:

(3S,4R,5R,αR)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol (1429412-87-2) + sodium hydrogencarbonate (144-55-8) → (2R,3R,4S,5S)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxypiperidine (1429413-06-8) + C30H43NO5Si (1429413-18-2) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With iodine; In 1,4-dioxane; water; at 20 ℃; for 16h;

DOI:10.1021/ol400735z

Reference yield:

2-benzyloxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(triisopropylsilyloxy)butanal (1429412-84-9) → (2R,3R,4S,5S)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxypiperidine (1429413-06-8) + C30H43NO5Si (1429413-18-2) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

2: iodine / water; 1,4-dioxane / 16 h / 20 °C

With iodine; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/ol400735z

upstream raw materials:

(2R,3R,4S,5S)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-diacetoxypiperidine

2-benzyloxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(triisopropylsilyloxy)butanal

C₃₅H₅₁NO₃Si

(3S,4R,5R,αR)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol

Downstream raw materials:

(2R,3R,4S,5S)-N⁽¹⁾-benzyl-2-(hydroxymethyl)-3-benzyloxy-4,5-dihydroxypiperidine

(2R,3R,4S,5S)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-diacetoxypiperidine