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

Base Information

• Chemical Name: (2R,3R,4S,5S)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-diacetoxypiperidine
• CAS No.: 1429413-08-0
• Molecular Formula: C₃₃H₄₉NO₆Si
• Molecular Weight: 583.841

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

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

Chemical Property:

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

There total 4 articles about (2R,3R,4S,5S)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-diacetoxypiperidine 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: 43.0%

(2R,3R,4S,5S)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxypiperidine (1429413-06-8) + acetic anhydride (108-24-7) → (2R,3R,4S,5S)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-diacetoxypiperidine (1429413-08-0)

Guidance literature:

With pyridine; dmap; at 0 - 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-diacetoxypiperidine (1429413-08-0)

Guidance literature:

Multi-step reaction with 3 steps

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

2.1: iodine; sodium hydrogencarbonate / water; 1,4-dioxane / 16 h / 20 °C

2.2: 16 h / 20 °C

3.1: pyridine; dmap / 16 h / 0 - 20 °C

With pyridine; dmap; iodine; sodium hydrogencarbonate; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/ol400735z

Reference yield:

C35H51NO3Si (1429412-83-8) → (2R,3R,4S,5S)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-diacetoxypiperidine (1429413-08-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.5 h / -78 °C

1.2: 0.5 h / -78 °C

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

3.1: iodine; sodium hydrogencarbonate / water; 1,4-dioxane / 16 h / 20 °C

3.2: 16 h / 20 °C

4.1: pyridine; dmap / 16 h / 0 - 20 °C

With pyridine; dmap; oxalyl dichloride; iodine; sodium hydrogencarbonate; dimethyl sulfoxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1021/ol400735z

upstream raw materials:

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

acetic anhydride

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

C₃₅H₅₁NO₃Si

Downstream raw materials:

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

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

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