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

Base Information

• Chemical Name: (R,R,R,R)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxypiperidine
• CAS No.: 1429412-98-5
• Molecular Formula: C₂₉H₄₅NO₄Si
• Molecular Weight: 499.766
• Mol file: 1429412-98-5.mol

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

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

There total 8 articles about (R,R,R,R)-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%

(R,R,R,R)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxy-4,5-O-carbonylpiperidine (1429412-96-3) → (R,R,R,R)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxypiperidine (1429412-98-5)

Guidance literature:

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

DOI:10.1021/ol400735z

Reference yield:

(1S,2R,3R,4R,5S)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-1-azabicyclo[3.1.0]hexanium tetrafluoroborate → (R,R,R,R)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxypiperidine (1429412-98-5) + C29H45NO4Si (1609168-88-8)

Guidance literature:

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

DOI:10.1016/j.tet.2014.03.100

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-4,5-dihydroxypiperidine (1429412-98-5)

Guidance literature:

Multi-step reaction with 3 steps

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

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

2.2: 16 h / 0 - 20 °C

3.1: potassium carbonate / methanol / 16 h / 20 °C

With iodine; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; water;

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

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

Downstream raw materials:

1-deoxymannojirimycin

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