(R,R,R,R)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-5-(iodomethyl)pyrrolidine

Base Information

• Chemical Name: (R,R,R,R)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-5-(iodomethyl)pyrrolidine
• CAS No.: 1429412-90-7
• Molecular Formula: C₂₉H₄₄INO₃Si
• Molecular Weight: 609.663

Synonyms:(R,R,R,R)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-5-(iodomethyl)pyrrolidine

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

Chemical Property:

Purity/Quality:

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

There total 3 articles about (R,R,R,R)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-5-(iodomethyl)pyrrolidine 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: 20.0%

(R,R,R,R)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol (1429412-85-0) → (R,R,R,R)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-5-(iodomethyl)pyrrolidine (1429412-90-7)

Guidance literature:

With iodine; sodium hydrogencarbonate; In acetonitrile; at 20 ℃; for 16h;

DOI:10.1021/ol400735z

Reference yield:

C35H51NO3Si (1429412-83-8) → (R,R,R,R)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-5-(iodomethyl)pyrrolidine (1429412-90-7)

Guidance literature:

Multi-step reaction with 3 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 / acetonitrile / 16 h / 20 °C

With oxalyl dichloride; iodine; sodium hydrogencarbonate; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ol400735z

Reference yield:

2-benzyloxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(triisopropylsilyloxy)butanal (1429412-84-9) → (R,R,R,R)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-5-(iodomethyl)pyrrolidine (1429412-90-7)

Guidance literature:

Multi-step reaction with 2 steps

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

2: iodine; sodium hydrogencarbonate / acetonitrile / 16 h / 20 °C

With iodine; sodium hydrogencarbonate; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ol400735z

upstream raw materials:

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

C₃₅H₅₁NO₃Si

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

Downstream raw materials:

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

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

1-deoxymannojirimycin

(R,R,R,R)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxy-4,5-O-carbonylpiperidine

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