(2R,3S,5S)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-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-hydroxy-7-(4-methoxy-benzyloxy)-heptan-1-one

Base Information

• Chemical Name: (2R,3S,5S)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-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-hydroxy-7-(4-methoxy-benzyloxy)-heptan-1-one
• CAS No.: 325172-31-4
• Molecular Formula: C₃₄H₅₅NO₇SSi
• Molecular Weight: 649.965

Synonyms:(2R,3S,5S)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-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-hydroxy-7-(4-methoxy-benzyloxy)-heptan-1-one

Chemical Property of (2R,3S,5S)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-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-hydroxy-7-(4-methoxy-benzyloxy)-heptan-1-one

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Technology Process of (2R,3S,5S)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-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-hydroxy-7-(4-methoxy-benzyloxy)-heptan-1-one

There total 5 articles about (2R,3S,5S)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-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-hydroxy-7-(4-methoxy-benzyloxy)-heptan-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: 95.0%

1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)pent-4-en-1-one (127392-82-9) + (S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)pentanal (325172-30-3) → (2R,3S,5S)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-hydroxy-7-(4-methoxy-benzyloxy)-heptan-1-one (325172-31-4)

Guidance literature:

1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)pent-4-en-1-one; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃;

(S)-3-((tert-butyl)dimethylsilyloxy)-5-(4-methoxybenzyloxy)pentanal; In dichloromethane; at -78 ℃;

DOI:10.1002/1521-3773(20001201)39:23<4308::AID-ANIE4308>3.0.CO;2-4

Reference yield:

3-(p-methoxybenzyloxy)propanal (128461-65-4) → (2R,3S,5S)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-hydroxy-7-(4-methoxy-benzyloxy)-heptan-1-one (325172-31-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diethyl ether / -78 °C

1.2: 96 percent / NaOOH / diethyl ether

2.1: 94 percent / imidazole; DMAP / dimethylformamide

3.1: 4-methylmorpholine N-oxide; aq. OsO₄ / acetone

4.1: Pb(OAc)4; pyridine / benzene

5.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / -78 °C

5.2: 95 percent / CH₂Cl₂ / -78 °C

With pyridine; 1H-imidazole; lead(IV) acetate; dmap; osmium(VIII) oxide; titanium tetrachloride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1002/1521-3773(20001201)39:23<4308::AID-ANIE4308>3.0.CO;2-4

Reference yield:

(3R)-1-[(4-methoxybenzyl)oxy]hex-5-en-3-ol (325172-29-0) → (2R,3S,5S)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-hydroxy-7-(4-methoxy-benzyloxy)-heptan-1-one (325172-31-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 94 percent / imidazole; DMAP / dimethylformamide

2.1: 4-methylmorpholine N-oxide; aq. OsO₄ / acetone

3.1: Pb(OAc)4; pyridine / benzene

4.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / -78 °C

4.2: 95 percent / CH₂Cl₂ / -78 °C

With pyridine; 1H-imidazole; lead(IV) acetate; dmap; osmium(VIII) oxide; titanium tetrachloride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1002/1521-3773(20001201)39:23<4308::AID-ANIE4308>3.0.CO;2-4

upstream raw materials:

1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)pent-4-en-1-one

(S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)pentanal

3-(p-methoxybenzyloxy)propanal

(3R)-1-[(4-methoxybenzyl)oxy]hex-5-en-3-ol

Downstream raw materials:

toluene-4-sulfonic acid 2-[3-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-1-methoxymethoxy-pentyl]-pent-4-enyl ester

2-Allyl-6-methoxy-benzoic acid (1R,3S,4R)-1-[2-(4-methoxy-benzyloxy)-ethyl]-3-methoxymethoxy-4-methyl-hept-6-enyl ester

(7R,9S,10R)-4-methoxy-7-[2-(4-methoxy-benzyloxy)-ethyl]-9-methoxymethoxy-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclododecen-5-one

2-[3-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-1-methoxymethoxy-pentyl]-pent-4-en-1-ol

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