(S)-5-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentan-2-one

Base Information

• Chemical Name: (S)-5-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentan-2-one
• CAS No.: 120341-90-4
• Molecular Formula: C₃₇H₅₄O₇Si
• Molecular Weight: 638.917

Synonyms:(S)-5-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentan-2-one

Chemical Property of (S)-5-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentan-2-one

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Technology Process of (S)-5-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentan-2-one

There total 15 articles about (S)-5-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentan-2-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: 69.0%

(S)-1-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-3-[2-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-[1,3]dithian-2-yl]-propan-2-ol (120341-89-1) → (S)-5-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentan-2-one (120341-90-4)

Guidance literature:

With 2,6-dimethylpyridine; N-Bromosuccinimide; silver nitrate; In water; acetonitrile; for 0.116667h;

DOI:10.1016/S0040-4039(00)82885-3

Reference yield:

(2S)-O-(tert-butyldiphenylsilyl)-1,2-epoxybutan-4-ol (125975-53-3,147220-48-2,116996-54-4) → (S)-5-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentan-2-one (120341-90-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) n-BuLi / 1.) THF, -20 deg C, 2 h, 2.) 17 h

2: 78 percent / NBS, AgNO₃, 2,6-lutidine / H₂O; acetonitrile / 0.12 h

3: LiAlH₄, LiI / diethyl ether / 0.5 h / -100 °C

4: 93 percent / PPTS / CH₂Cl₂ / 7 h

5: 42 percent / acetic acid; tetrahydrofuran / 48 h / -10 °C

6: pyridine / 3 h / 0 °C

7: KH / diethyl ether; methanol / 0.33 h / 0 °C

8: 1.) n-BuLi / 1.) THF, -20 deg C, 2h, 2.) 9 h

9: 69 percent / NBS, AgNO₃, 2,6-lutidine / H₂O; acetonitrile / 0.12 h

With pyridine; 2,6-dimethylpyridine; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; pyridinium p-toluenesulfonate; potassium hydride; silver nitrate; lithium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; acetonitrile;

DOI:10.1016/S0040-4039(00)82885-3

Reference yield:

(2S)-4-O-(tert-butyldiphenylsilyl)butane-1,2,4-triol (116996-52-2) → (S)-5-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentan-2-one (120341-90-4)

Guidance literature:

Multi-step reaction with 11 steps

1: pyridine

2: K₂CO₃ / methanol

3: 1.) n-BuLi / 1.) THF, -20 deg C, 2 h, 2.) 17 h

4: 78 percent / NBS, AgNO₃, 2,6-lutidine / H₂O; acetonitrile / 0.12 h

5: LiAlH₄, LiI / diethyl ether / 0.5 h / -100 °C

6: 93 percent / PPTS / CH₂Cl₂ / 7 h

7: 42 percent / acetic acid; tetrahydrofuran / 48 h / -10 °C

8: pyridine / 3 h / 0 °C

9: KH / diethyl ether; methanol / 0.33 h / 0 °C

10: 1.) n-BuLi / 1.) THF, -20 deg C, 2h, 2.) 9 h

11: 69 percent / NBS, AgNO₃, 2,6-lutidine / H₂O; acetonitrile / 0.12 h

With pyridine; 2,6-dimethylpyridine; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; pyridinium p-toluenesulfonate; potassium hydride; potassium carbonate; silver nitrate; lithium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; acetonitrile;

DOI:10.1016/S0040-4039(00)82885-3

upstream raw materials:

(S)-1-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-3-[2-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-[1,3]dithian-2-yl]-propan-2-ol

(2S)-O-(tert-butyldiphenylsilyl)-1,2-epoxybutan-4-ol

(2S)-4-O-(tert-butyldiphenylsilyl)butane-1,2,4-triol

2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde

Downstream raw materials:

(2R,4S)-1-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-2,4-diol

(2S,4S,6S,8S,10S)-12-(tert-Butyl-diphenyl-silanyloxy)-dodecane-1,2,4,6,8,10-hexaol

tert-Butyl-(2-{(2S,4S)-4-[(2S,4S)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1,5-dioxa-spiro[5.5]undec-2-ylmethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-ethoxy)-diphenyl-silane

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