(1S,2R,3S,6R,7S,8R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-7-methoxy-8-methyl-5,9-dioxa-tricyclo[6.2.1.0^2,6]undecan-10-one

Base Information

• Chemical Name: (1S,2R,3S,6R,7S,8R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-7-methoxy-8-methyl-5,9-dioxa-tricyclo[6.2.1.0^2,6]undecan-10-one
• CAS No.: 114247-53-9
• Molecular Formula: C₂₇H₃₄O₆Si
• Molecular Weight: 482.649

Synonyms:(1S,2R,3S,6R,7S,8R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-7-methoxy-8-methyl-5,9-dioxa-tricyclo[6.2.1.0^2,6]undecan-10-one

Chemical Property of (1S,2R,3S,6R,7S,8R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-7-methoxy-8-methyl-5,9-dioxa-tricyclo[6.2.1.0^2,6]undecan-10-one

Chemical Property:

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Technology Process of (1S,2R,3S,6R,7S,8R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-7-methoxy-8-methyl-5,9-dioxa-tricyclo[6.2.1.0^2,6]undecan-10-one

There total 16 articles about (1S,2R,3S,6R,7S,8R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-7-methoxy-8-methyl-5,9-dioxa-tricyclo[6.2.1.0^2,6]undecan-10-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: 85.0%

C27H34O6Si (114158-41-7,114158-42-8) → (1S,2R,3S,6R,7S,8R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-7-methoxy-8-methyl-5,9-dioxa-tricyclo[6.2.1.02,6]undecan-10-one (114247-53-9)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/0040-4039(88)85177-3

Reference yield:

(R)-2-[(2R,3S,4S)-3-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-2-methoxy-ethanol → (1S,2R,3S,6R,7S,8R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-7-methoxy-8-methyl-5,9-dioxa-tricyclo[6.2.1.02,6]undecan-10-one (114247-53-9)

Guidance literature:

Multi-step reaction with 9 steps

1: PCC-Al₂O₃ / -60 °C

2: 83 percent / tetrahydrofuran / -78 °C

3: 79 percent / PCC-Al₂O₃

4: tetrahydrofuran / -78 °C

5: 1.) O₃, pyridine, 2.) Ph₃P / 1.) CH₂Cl₂; 2.) CH₂Cl₂

6: PCC-Al₂O₃

7: H₂ / Pd-black / ethanol

8: PCC-Al₂O₃ / CH₂Cl₂

9: 85 percent / LDA / tetrahydrofuran / -78 °C

With pyridine; pyridinium chlorochromate absorbed on neutral alumina; hydrogen; ozone; triphenylphosphine; lithium diisopropyl amide; palladium; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/0040-4039(88)85177-3

Reference yield:

(S)-[(2S,3S,4S)-3-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-methoxy-acetaldehyde (119841-62-2) → (1S,2R,3S,6R,7S,8R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-7-methoxy-8-methyl-5,9-dioxa-tricyclo[6.2.1.02,6]undecan-10-one (114247-53-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 83 percent / tetrahydrofuran / -78 °C

2: 79 percent / PCC-Al₂O₃

3: tetrahydrofuran / -78 °C

4: 1.) O₃, pyridine, 2.) Ph₃P / 1.) CH₂Cl₂; 2.) CH₂Cl₂

5: PCC-Al₂O₃

6: H₂ / Pd-black / ethanol

7: PCC-Al₂O₃ / CH₂Cl₂

8: 85 percent / LDA / tetrahydrofuran / -78 °C

With pyridine; pyridinium chlorochromate absorbed on neutral alumina; hydrogen; ozone; triphenylphosphine; lithium diisopropyl amide; palladium; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/0040-4039(88)85177-3

upstream raw materials:

C₂₇H₃₄O₆Si

(S)-[(2S,3S,4S)-3-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-methoxy-acetaldehyde

(S)-1-[(2S,3S,4S)-3-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-1-methoxy-propan-2-one

Benzoic acid (R)-2-[(2R,3S,4S)-3-benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-2-hydroxy-ethyl ester

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