(2S,3S)-2-((R)-2-Benzyloxy-1-hydroxy-ethyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-methyl-pentan-1-one

Base Information

• Chemical Name: (2S,3S)-2-((R)-2-Benzyloxy-1-hydroxy-ethyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-methyl-pentan-1-one
• CAS No.: 873309-31-0
• Molecular Formula: C₂₅H₃₇NO₅S
• Molecular Weight: 463.638

Synonyms:(2S,3S)-2-((R)-2-Benzyloxy-1-hydroxy-ethyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-methyl-pentan-1-one

Chemical Property of (2S,3S)-2-((R)-2-Benzyloxy-1-hydroxy-ethyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-methyl-pentan-1-one

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Technology Process of (2S,3S)-2-((R)-2-Benzyloxy-1-hydroxy-ethyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-methyl-pentan-1-one

There total 3 articles about (2S,3S)-2-((R)-2-Benzyloxy-1-hydroxy-ethyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-methyl-pentan-1-one 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: 67.0%

benzyloxyacetoaldehyde (60656-87-3) + (S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-methyl-pentan-1-one (108509-67-7) → (2R,3S)-2-((R)-2-Benzyloxy-1-hydroxy-ethyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-methyl-pentan-1-one + (2S,3S)-2-((R)-2-Benzyloxy-1-hydroxy-ethyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-methyl-pentan-1-one (873309-31-0)

Guidance literature:

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1021/jo0516887

Reference yield:

(S)-3-methylpentanoic acid chloride (28977-69-7) → (2S,3S)-2-((R)-2-Benzyloxy-1-hydroxy-ethyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-methyl-pentan-1-one (873309-31-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / CuCl₂ / benzene / 4 h / Heating

2: 67 percent / TiCl₄; (i-Pr₂)NEt / CH₂Cl₂ / 3 h / 0 °C

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; copper dichloride; In dichloromethane; benzene;

DOI:10.1021/jo0516887

Reference yield:

(2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) → (2S,3S)-2-((R)-2-Benzyloxy-1-hydroxy-ethyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-methyl-pentan-1-one (873309-31-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / CuCl₂ / benzene / 4 h / Heating

2: 67 percent / TiCl₄; (i-Pr₂)NEt / CH₂Cl₂ / 3 h / 0 °C

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; copper dichloride; In dichloromethane; benzene;

DOI:10.1021/jo0516887

upstream raw materials:

benzyloxyacetoaldehyde

(S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-methyl-pentan-1-one

(S)-3-methylpentanoic acid chloride

(2R)-bornane-10,2-sultam

Downstream raw materials:

(3R,2R)-4-benzyloxy-2-((S)-sec-butyl)butane-1,3-diol

(2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}pentanoic acid benzyl ester

(2S,3S)-2-((R)-2-Benzyloxy-1-hydroxy-ethyl)-3-methyl-pentanoic acid

(3S,4R)-4-benzyloxymethyl-3-((S)-sec-butyl)oxetan-2-one

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