(S)-5-{(S)-[(2S,3S,4S)-3-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-methoxy-methyl}-5-methyl-dihydro-furan-2-one

Base Information

• Chemical Name: (S)-5-{(S)-[(2S,3S,4S)-3-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-methoxy-methyl}-5-methyl-dihydro-furan-2-one
• CAS No.: 119841-65-5
• Molecular Formula: C₃₄H₄₂O₆Si
• Molecular Weight: 574.789

Synonyms:(S)-5-{(S)-[(2S,3S,4S)-3-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-methoxy-methyl}-5-methyl-dihydro-furan-2-one

Chemical Property of (S)-5-{(S)-[(2S,3S,4S)-3-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-methoxy-methyl}-5-methyl-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (S)-5-{(S)-[(2S,3S,4S)-3-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-methoxy-methyl}-5-methyl-dihydro-furan-2-one

There total 30 articles about (S)-5-{(S)-[(2S,3S,4S)-3-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-methoxy-methyl}-5-methyl-dihydro-furan-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:

benzyl bromide (100-39-0) → (R)-5-{(S)-[(2S,3S,4S)-3-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-methoxy-methyl}-5-methyl-dihydro-furan-2-one (119841-65-5)

Guidance literature:

Multi-step reaction with 11 steps

1: NaH / tetrahydrofuran / 0 - 22 °C

2: p-TsOH / methanol / 14 h / 22 °C

3: Et₃N, DMAP / CH₂Cl₂ / -78 - -40 °C

4: NaH / dimethylformamide / 0 °C

5: LiOH, H₂O / tetrahydrofuran

6: PCC-Al₂O₃ / -60 °C

7: 83 percent / tetrahydrofuran / -78 °C

8: 79 percent / PCC-Al₂O₃

9: tetrahydrofuran / -78 °C

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

11: PCC-Al₂O₃

With pyridine; dmap; lithium hydroxide; pyridinium chlorochromate absorbed on neutral alumina; water; sodium hydride; toluene-4-sulfonic acid; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

(2S,3R,4S)-2-((S)-4,4-Dimethyl-[1,3]dioxolan-2-yl)-tetrahydro-furan-3,4-diol → (R)-5-{(S)-[(2S,3S,4S)-3-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-methoxy-methyl}-5-methyl-dihydro-furan-2-one (119841-65-5)

Guidance literature:

Multi-step reaction with 12 steps

1: Et₃N, DMAP / CH₂Cl₂ / -10 - 22 °C

2: NaH / tetrahydrofuran / 0 - 22 °C

3: p-TsOH / methanol / 14 h / 22 °C

4: Et₃N, DMAP / CH₂Cl₂ / -78 - -40 °C

5: NaH / dimethylformamide / 0 °C

6: LiOH, H₂O / tetrahydrofuran

7: PCC-Al₂O₃ / -60 °C

8: 83 percent / tetrahydrofuran / -78 °C

9: 79 percent / PCC-Al₂O₃

10: tetrahydrofuran / -78 °C

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

12: PCC-Al₂O₃

With pyridine; dmap; lithium hydroxide; pyridinium chlorochromate absorbed on neutral alumina; water; sodium hydride; toluene-4-sulfonic acid; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

(2S,3S,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-((S)-4,4-dimethyl-[1,3]dioxolan-2-yl)-tetrahydro-furan-3-ol → (R)-5-{(S)-[(2S,3S,4S)-3-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-methoxy-methyl}-5-methyl-dihydro-furan-2-one (119841-65-5)

Guidance literature:

Multi-step reaction with 11 steps

1: NaH / tetrahydrofuran / 0 - 22 °C

2: p-TsOH / methanol / 14 h / 22 °C

3: Et₃N, DMAP / CH₂Cl₂ / -78 - -40 °C

4: NaH / dimethylformamide / 0 °C

5: LiOH, H₂O / tetrahydrofuran

6: PCC-Al₂O₃ / -60 °C

7: 83 percent / tetrahydrofuran / -78 °C

8: 79 percent / PCC-Al₂O₃

9: tetrahydrofuran / -78 °C

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

11: PCC-Al₂O₃

With pyridine; dmap; lithium hydroxide; pyridinium chlorochromate absorbed on neutral alumina; water; sodium hydride; toluene-4-sulfonic acid; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

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

upstream raw materials:

benzyl bromide

(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

Downstream raw materials:

(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

C₂₇H₃₄O₆Si

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

C₂₇H₃₄O₆Si

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