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

Base Information

• Chemical Name: (3S,4R,5R,αR)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol
• CAS No.: 1429412-87-2
• Molecular Formula: C₃₇H₅₃NO₃Si
• Molecular Weight: 587.918
• Mol file: 1429412-87-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (3S,4R,5R,αR)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol 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: 55.0%

2-benzyloxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(triisopropylsilyloxy)butanal (1429412-84-9) + vinyl magnesium bromide (1826-67-1) → (R,R,R,R)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol (1429412-85-0) + (3S,4R,5R,αR)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol (1429412-87-2)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ol400735z

Reference yield:

C35H51NO3Si (1429412-83-8) → (3S,4R,5R,αR)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol (1429412-87-2)

Guidance literature:

Multi-step reaction with 2 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

With oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol400735z

Reference yield: 48.0%

(3S,4R,5R,αR)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol (1429412-87-2) + Tosyl isocyanate (4083-64-1) + sodium hydrogencarbonate (144-55-8) → (2R,3R,4S,5S)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-5-(N-tosylamino)-4,5-O,N-carbonylpiperidine

Guidance literature:

(3S,4R,5R,αR)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol; sodium hydrogencarbonate; In acetonitrile; at 20 ℃; for 16h;

Tosyl isocyanate; In acetonitrile; at 20 ℃; for 16h;

DOI:10.1021/acs.joc.6b01107

upstream raw materials:

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

vinyl magnesium bromide

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-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-diacetoxypiperidine

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

C₃₀H₄₃NO₅Si