(2R,3S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,3-dihydroxy-3-phenyl-propan-1-one

Base Information

• Chemical Name: (2R,3S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,3-dihydroxy-3-phenyl-propan-1-one
• CAS No.: 212690-64-7
• Molecular Formula: C₁₉H₂₅NO₅S
• Molecular Weight: 379.477

Synonyms:(2R,3S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,3-dihydroxy-3-phenyl-propan-1-one

Chemical Property of (2R,3S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,3-dihydroxy-3-phenyl-propan-1-one

Chemical Property:

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Technology Process of (2R,3S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,3-dihydroxy-3-phenyl-propan-1-one

There total 3 articles about (2R,3S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,3-dihydroxy-3-phenyl-propan-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:

(3aS,6R,7aR)-8,8-dimethyl-1-[(2E)-3-phenylprop-2-enoyl]hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide (109053-73-8,138381-27-8,143167-59-3) → (2R,3S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2,3-dihydroxy-3-phenyl-propan-1-one (212690-64-7) + (2S,3R)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2,3-dihydroxy-3-phenyl-propan-1-one

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In N,N-dimethyl-formamide; tert-butyl alcohol; at 0 ℃; for 4h; Yield given;

DOI:10.1002/hlca.19980810537

Reference yield:

Cinnamoyl chloride (102-92-1,17082-09-6) → (2R,3S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2,3-dihydroxy-3-phenyl-propan-1-one (212690-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / AgCN / toluene / 8 h / Heating

2: 4-methylmorpholine-4-oxide, OsO₄ / 2-methyl-propan-2-ol; dimethylformamide / 4 h / 0 °C

With osmium(VIII) oxide; silver cyanide; 4-methylmorpholine N-oxide; In N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1002/hlca.19980810537

Reference yield:

(2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) → (2R,3S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2,3-dihydroxy-3-phenyl-propan-1-one (212690-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / AgCN / toluene / 8 h / Heating

2: 4-methylmorpholine-4-oxide, OsO₄ / 2-methyl-propan-2-ol; dimethylformamide / 4 h / 0 °C

With osmium(VIII) oxide; silver cyanide; 4-methylmorpholine N-oxide; In N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1002/hlca.19980810537

upstream raw materials:

(3aS,6R,7aR)-8,8-dimethyl-1-[(2E)-3-phenylprop-2-enoyl]hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide

Cinnamoyl chloride

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

Downstream raw materials:

methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate

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