(S)-1-[(2S,5R)-5-((1S,2S,3S)-3-{(2S,5R)-5-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-furan-2-yl}-2-hydroxy-1-methyl-butyl)-tetrahydro-furan-2-yl]-pentan-2-ol

Base Information

• Chemical Name: (S)-1-[(2S,5R)-5-((1S,2S,3S)-3-{(2S,5R)-5-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-furan-2-yl}-2-hydroxy-1-methyl-butyl)-tetrahydro-furan-2-yl]-pentan-2-ol
• CAS No.: 452085-31-3
• Molecular Formula: C₃₇H₅₈O₅Si
• Molecular Weight: 610.95
• Mol file: 452085-31-3.mol

Synonyms:(S)-1-[(2S,5R)-5-((1S,2S,3S)-3-{(2S,5R)-5-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-furan-2-yl}-2-hydroxy-1-methyl-butyl)-tetrahydro-furan-2-yl]-pentan-2-ol

Chemical Property of (S)-1-[(2S,5R)-5-((1S,2S,3S)-3-{(2S,5R)-5-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-furan-2-yl}-2-hydroxy-1-methyl-butyl)-tetrahydro-furan-2-yl]-pentan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-[(2S,5R)-5-((1S,2S,3S)-3-{(2S,5R)-5-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-furan-2-yl}-2-hydroxy-1-methyl-butyl)-tetrahydro-furan-2-yl]-pentan-2-ol

There total 37 articles about (S)-1-[(2S,5R)-5-((1S,2S,3S)-3-{(2S,5R)-5-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-furan-2-yl}-2-hydroxy-1-methyl-butyl)-tetrahydro-furan-2-yl]-pentan-2-ol 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%

C50H78O5Si2 (452085-30-2) → (S)-1-[(2S,5R)-5-((1S,2S,3S)-3-{(2S,5R)-5-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-furan-2-yl}-2-hydroxy-1-methyl-butyl)-tetrahydro-furan-2-yl]-pentan-2-ol (452085-31-3)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; at 20 ℃;

DOI:10.1016/S0040-4039(02)00655-X

Reference yield:

(S)-Pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-[1-(3-benzyloxy-propyl)-3,4-dihydroxy-2-methyl-butyl] ester → (S)-1-[(2S,5R)-5-((1S,2S,3S)-3-{(2S,5R)-5-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-furan-2-yl}-2-hydroxy-1-methyl-butyl)-tetrahydro-furan-2-yl]-pentan-2-ol (452085-31-3)

Guidance literature:

Multi-step reaction with 25 steps

1.1: NaIO₄ / tetrahydrofuran; H₂O / 20 °C

2.1: NaBH₄ / tetrahydrofuran; H₂O / 0 °C

3.1: LiOH; H₂O / methanol / 20 °C

4.1: PPTS / toluene / Heating

5.1: Li; liq. NH₃ / tetrahydrofuran / -78 °C

6.1: Ph₃P; I₂; imidazole / tetrahydrofuran / 0 °C

7.1: cc. HCl / methanol / 0 °C

8.1: DMAP; Et₃N / CH₂Cl₂ / -15 °C

9.1: DMAP; Et₃N / CH₂Cl₂ / -15 °C

10.1: K₂CO₃ / acetonitrile / Heating

11.1: t-BuLi / tetrahydrofuran / -78 - -5 °C

11.2: tetrahydrofuran / 10 °C

12.1: 94 percent / Ag₂CO₃; I₂ / diethyl ether / 20 °C

13.1: PPTS / methanol; tetrahydrofuran / 20 °C

13.2: K₂CO₃ / tetrahydrofuran; methanol / 20 °C

14.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

15.1: 78 percent / diethyl ether / 10 °C

16.1: 96 percent / H₂ / Pd(OH)2/C / ethanol / 20 °C

17.1: PPTS / 20 °C

18.1: I₂; Ph₃P; imidazole / tetrahydrofuran / 0 °C

19.1: K₂CO₃ / acetonitrile / Heating

20.1: n-BuLi / tetrahydrofuran / -78 - -5 °C

20.2: 88 percent / tetrahydrofuran / 10 °C

21.1: PPTS; MeOH / tetrahydrofuran / 20 °C

22.1: 2,6-lutidine / CH₂Cl₂ / 20 °C

23.1: I₂; Ag₂CO₃ / diethyl ether / 20 °C

24.1: Ph₃SnH; Et₃B / tetrahydrofuran / 0 °C

25.1: 95 percent / H₂ / Pd(OH)2/C / ethanol / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; methanol; dmap; lithium hydroxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; triethyl borane; triphenylstannane; ammonia; water; hydrogen; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; lithium; potassium carbonate; triethylamine; triphenylphosphine; silver carbonate; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; toluene; acetonitrile; 11.2: Wittig olefination;

DOI:10.1016/S0040-4039(02)00655-X

Reference yield:

7-benzyloxy-3-methyl-hept-1-en-4-ol → (S)-1-[(2S,5R)-5-((1S,2S,3S)-3-{(2S,5R)-5-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-furan-2-yl}-2-hydroxy-1-methyl-butyl)-tetrahydro-furan-2-yl]-pentan-2-ol (452085-31-3)

Guidance literature:

Multi-step reaction with 27 steps

1.1: DCC; DMAP / CH₂Cl₂ / 20 °C

2.1: OsO₄; NMO / acetone; H₂O / 20 °C

3.1: NaIO₄ / tetrahydrofuran; H₂O / 20 °C

4.1: NaBH₄ / tetrahydrofuran; H₂O / 0 °C

5.1: LiOH; H₂O / methanol / 20 °C

6.1: PPTS / toluene / Heating

7.1: Li; liq. NH₃ / tetrahydrofuran / -78 °C

8.1: Ph₃P; I₂; imidazole / tetrahydrofuran / 0 °C

9.1: cc. HCl / methanol / 0 °C

10.1: DMAP; Et₃N / CH₂Cl₂ / -15 °C

11.1: DMAP; Et₃N / CH₂Cl₂ / -15 °C

12.1: K₂CO₃ / acetonitrile / Heating

13.1: t-BuLi / tetrahydrofuran / -78 - -5 °C

13.2: tetrahydrofuran / 10 °C

14.1: 94 percent / Ag₂CO₃; I₂ / diethyl ether / 20 °C

15.1: PPTS / methanol; tetrahydrofuran / 20 °C

15.2: K₂CO₃ / tetrahydrofuran; methanol / 20 °C

16.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

17.1: 78 percent / diethyl ether / 10 °C

18.1: 96 percent / H₂ / Pd(OH)2/C / ethanol / 20 °C

19.1: PPTS / 20 °C

20.1: I₂; Ph₃P; imidazole / tetrahydrofuran / 0 °C

21.1: K₂CO₃ / acetonitrile / Heating

22.1: n-BuLi / tetrahydrofuran / -78 - -5 °C

22.2: 88 percent / tetrahydrofuran / 10 °C

23.1: PPTS; MeOH / tetrahydrofuran / 20 °C

24.1: 2,6-lutidine / CH₂Cl₂ / 20 °C

25.1: I₂; Ag₂CO₃ / diethyl ether / 20 °C

26.1: Ph₃SnH; Et₃B / tetrahydrofuran / 0 °C

27.1: 95 percent / H₂ / Pd(OH)2/C / ethanol / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; methanol; dmap; lithium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; triethyl borane; triphenylstannane; ammonia; water; hydrogen; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; lithium; potassium carbonate; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; silver carbonate; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; acetonitrile; 13.2: Wittig olefination;

DOI:10.1016/S0040-4039(02)00655-X

upstream raw materials:

C₅₀H₇₈O₅Si₂

(2R,3S)-1,2-O-isopropylidene-hexane-1,2,3-triol

(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

(2S,3R)-6-(benzyloxy)-2-methylhexane-1,3-diol

Downstream raw materials:

((S)-2-{(2R,5S)-5-[(1R,2S,3R)-3-[(2R,5S)-5-((R)-2-Azido-pentyl)-tetrahydro-furan-2-yl]-2-(4-methoxy-benzyloxy)-1-methyl-butyl]-tetrahydro-furan-2-yl}-propoxy)-tert-butyl-diphenyl-silane