((2S,3R,6S)-6-{(S)-1-Benzyloxy-3-[(4S,5S)-2,2-dimethyl-5-(3-oxo-propyl)-[1,3]dioxolan-4-yl]-propyl}-3-hydroxy-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

Base Information

• Chemical Name: ((2S,3R,6S)-6-{(S)-1-Benzyloxy-3-[(4S,5S)-2,2-dimethyl-5-(3-oxo-propyl)-[1,3]dioxolan-4-yl]-propyl}-3-hydroxy-tetrahydro-pyran-2-yl)-acetic acid ethyl ester
• CAS No.: 500594-05-8
• Molecular Formula: C₂₇H₄₀O₈
• Molecular Weight: 492.61

Synonyms:((2S,3R,6S)-6-{(S)-1-Benzyloxy-3-[(4S,5S)-2,2-dimethyl-5-(3-oxo-propyl)-[1,3]dioxolan-4-yl]-propyl}-3-hydroxy-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

Chemical Property of ((2S,3R,6S)-6-{(S)-1-Benzyloxy-3-[(4S,5S)-2,2-dimethyl-5-(3-oxo-propyl)-[1,3]dioxolan-4-yl]-propyl}-3-hydroxy-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

Chemical Property:

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Technology Process of ((2S,3R,6S)-6-{(S)-1-Benzyloxy-3-[(4S,5S)-2,2-dimethyl-5-(3-oxo-propyl)-[1,3]dioxolan-4-yl]-propyl}-3-hydroxy-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

There total 9 articles about ((2S,3R,6S)-6-{(S)-1-Benzyloxy-3-[(4S,5S)-2,2-dimethyl-5-(3-oxo-propyl)-[1,3]dioxolan-4-yl]-propyl}-3-hydroxy-tetrahydro-pyran-2-yl)-acetic acid ethyl ester 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: 87.0%

(E)-3-[(1S,2S)-2-Benzyloxy-4-[(4S,5S)-2,2-dimethyl-5-(3-oxo-propyl)-[1,3]dioxolan-4-yl]-1-(3-oxo-propyl)-butoxy]-acrylic acid ethyl ester (500593-99-7) → ((2S,3R,6S)-6-{(S)-1-Benzyloxy-3-[(4S,5S)-2,2-dimethyl-5-(3-oxo-propyl)-[1,3]dioxolan-4-yl]-propyl}-3-hydroxy-tetrahydro-pyran-2-yl)-acetic acid ethyl ester (500594-05-8)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; methanol; at -5 ℃; for 0.25h;

DOI:10.1002/anie.200290038

Reference yield:

1,1,12,12-tetramethoxy-dodeca-4t,8t-diene (63284-80-0) → ((2S,3R,6S)-6-{(S)-1-Benzyloxy-3-[(4S,5S)-2,2-dimethyl-5-(3-oxo-propyl)-[1,3]dioxolan-4-yl]-propyl}-3-hydroxy-tetrahydro-pyran-2-yl)-acetic acid ethyl ester (500594-05-8)

Guidance literature:

Multi-step reaction with 8 steps

1: AD-mix-α; MeSO2NH2; H2O / 2-methyl-propan-2-ol / 24 h / 0 °C

2: 10-camphorsulfonic acid / methanol / 3 h / -5 °C

3: 93 percent / NaH / tetrahydrofuran / 16 h / -15 - 20 °C

4: Zn(OTf)2 / 1,2-dichloro-ethane / 2 h / 50 °C

5: 10-camphorsulfonic acid / CH₂Cl₂ / 1 h / 20 °C

6: N-methylmorpholine / CH₂Cl₂ / 5 h / 20 °C

7: MeI; aq. NaHCO₃ / acetonitrile / 35 h / 20 °C

8: 87 percent / SmI₂ / methanol; tetrahydrofuran / 0.25 h / -5 °C

With 4-methyl-morpholine; AD-mix-α; samarium diiodide; methanesulfonamide; (1S)-10-camphorsulfonic acid; water; zinc trifluoromethanesulfonate; sodium hydride; sodium hydrogencarbonate; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol; 1: Sharpless dihydroxylation / 6: hetero-Michael addition;

DOI:10.1002/anie.200290038

Reference yield:

(4E,8E)-dodeca-4,8-dienedial (60391-93-7) → ((2S,3R,6S)-6-{(S)-1-Benzyloxy-3-[(4S,5S)-2,2-dimethyl-5-(3-oxo-propyl)-[1,3]dioxolan-4-yl]-propyl}-3-hydroxy-tetrahydro-pyran-2-yl)-acetic acid ethyl ester (500594-05-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 99 percent / 10-camphorsulfonic acid / methanol / 1 h / 20 °C

2: AD-mix-α; MeSO2NH2; H2O / 2-methyl-propan-2-ol / 24 h / 0 °C

3: 10-camphorsulfonic acid / methanol / 3 h / -5 °C

4: 93 percent / NaH / tetrahydrofuran / 16 h / -15 - 20 °C

5: Zn(OTf)2 / 1,2-dichloro-ethane / 2 h / 50 °C

6: 10-camphorsulfonic acid / CH₂Cl₂ / 1 h / 20 °C

7: N-methylmorpholine / CH₂Cl₂ / 5 h / 20 °C

8: MeI; aq. NaHCO₃ / acetonitrile / 35 h / 20 °C

9: 87 percent / SmI₂ / methanol; tetrahydrofuran / 0.25 h / -5 °C

With 4-methyl-morpholine; AD-mix-α; samarium diiodide; methanesulfonamide; (1S)-10-camphorsulfonic acid; water; zinc trifluoromethanesulfonate; sodium hydride; sodium hydrogencarbonate; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol; 2: Sharpless dihydroxylation / 7: hetero-Michael addition;

DOI:10.1002/anie.200290038

upstream raw materials:

(E)-3-[(1S,2S)-2-Benzyloxy-4-[(4S,5S)-2,2-dimethyl-5-(3-oxo-propyl)-[1,3]dioxolan-4-yl]-1-(3-oxo-propyl)-butoxy]-acrylic acid ethyl ester

1,1,12,12-tetramethoxy-dodeca-4t,8t-diene

(4E,8E)-dodeca-4,8-dienedial

(1S,4S)-1,4-Bis-((S)-5-methoxy-tetrahydro-furan-2-yl)-butane-1,4-diol

Downstream raw materials:

(S)-3-((R)-2-(tert-Butyl-diphenyl-silanyloxy)-9-{(2R,5S)-5-[(1S,4S)-4-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-1,4-bis-methoxymethoxy-butyl]-tetrahydro-furan-2-yl}-nonyl)-5-methyl-5H-furan-2-one

(S)-3-((E)-(R)-2-(tert-Butyl-diphenyl-silanyloxy)-9-{(2S,5S)-5-[(1S,4S)-4-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-1,4-bis-methoxymethoxy-butyl]-tetrahydro-furan-2-yl}-non-5-en-7-ynyl)-5-methyl-5H-furan-2-one

(2S,3R,6S)-6-[(1S,4S)-1-Benzyloxy-4-methoxymethoxy-4-((S)-5-methoxy-tetrahydro-furan-2-yl)-butyl]-2-((Z)-dec-2-enyl)-3-methoxymethoxy-tetrahydro-pyran

{(2S,3R,6S)-6-[(1S,4S)-1-Benzyloxy-4-methoxymethoxy-4-((S)-5-methoxy-tetrahydro-furan-2-yl)-butyl]-3-methoxymethoxy-tetrahydro-pyran-2-yl}-acetic acid ethyl ester

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