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

Base Information

• Chemical Name: (R,R,R,R)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxy-4,5-O-carbonylpiperidine
• CAS No.: 1429412-96-3
• Molecular Formula: C₃₀H₄₃NO₅Si
• Molecular Weight: 525.761

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

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

Chemical Property:

Purity/Quality:

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

There total 8 articles about (R,R,R,R)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxy-4,5-O-carbonylpiperidine 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%

(1S,2R,3R,4R,5S)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-1-azabicyclo[3.1.0]hexanium tetrafluoroborate + sodium hydrogencarbonate (144-55-8) → (R,R,R,R)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxy-4,5-O-carbonylpiperidine (1429412-96-3)

Guidance literature:

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

DOI:10.1021/ol400735z

Reference yield: 48.0%

(R,R,R,R)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-5-(iodomethyl)pyrrolidine (1429412-90-7) + Tosyl isocyanate (4083-64-1) → (R,R,R,R)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxy-4,5-O-carbonylpiperidine (1429412-96-3) + C30H44N2O4Si + (R,R,R,R)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-5-(N-tosylamino)-4,5-O,N-carbonylpiperidine + C38H52N2O6SSi + C30H46INO3Si

Guidance literature:

(R,R,R,R)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-5-(iodomethyl)pyrrolidine; Tosyl isocyanate; In dichloromethane; at 20 ℃; for 0.0833333h;

With silver tetrafluoroborate; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/acs.joc.6b01107

Reference yield: 26.0%

(R,R,R,R)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol (1429412-85-0) + sodium hydrogencarbonate (144-55-8) → (R,R,R,R)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxy-4,5-O-carbonylpiperidine (1429412-96-3) + 1-phenylethyl acetate (93-92-5,50373-55-2)

Guidance literature:

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

With pyridine; dmap; acetic anhydride; at 0 - 20 ℃; for 16h;

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:

(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

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