(R)-2-((2R,3S,4S,6S,8S)-4,8-Bis-benzyloxy-2-ethyl-1,5-dioxa-spiro[2.5]oct-6-yl)-1-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,4-bis-methoxymethoxy-5-((R)-1-methoxy-2-methyl-propyl)-phenyl]-pentan-1-one

Base Information

• Chemical Name: (R)-2-((2R,3S,4S,6S,8S)-4,8-Bis-benzyloxy-2-ethyl-1,5-dioxa-spiro[2.5]oct-6-yl)-1-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,4-bis-methoxymethoxy-5-((R)-1-methoxy-2-methyl-propyl)-phenyl]-pentan-1-one
• CAS No.: 383125-20-0
• Molecular Formula: C₄₉H₇₂O₁₁Si
• Molecular Weight: 865.19
• Mol file: 383125-20-0.mol

Synonyms:(R)-2-((2R,3S,4S,6S,8S)-4,8-Bis-benzyloxy-2-ethyl-1,5-dioxa-spiro[2.5]oct-6-yl)-1-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,4-bis-methoxymethoxy-5-((R)-1-methoxy-2-methyl-propyl)-phenyl]-pentan-1-one

Chemical Property of (R)-2-((2R,3S,4S,6S,8S)-4,8-Bis-benzyloxy-2-ethyl-1,5-dioxa-spiro[2.5]oct-6-yl)-1-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,4-bis-methoxymethoxy-5-((R)-1-methoxy-2-methyl-propyl)-phenyl]-pentan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-((2R,3S,4S,6S,8S)-4,8-Bis-benzyloxy-2-ethyl-1,5-dioxa-spiro[2.5]oct-6-yl)-1-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,4-bis-methoxymethoxy-5-((R)-1-methoxy-2-methyl-propyl)-phenyl]-pentan-1-one

There total 36 articles about (R)-2-((2R,3S,4S,6S,8S)-4,8-Bis-benzyloxy-2-ethyl-1,5-dioxa-spiro[2.5]oct-6-yl)-1-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,4-bis-methoxymethoxy-5-((R)-1-methoxy-2-methyl-propyl)-phenyl]-pentan-1-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: 70.0%

tert-butyl-[3-iodo-2,6-bis-methoxymethoxy-5-(1-methoxy-2-methyl-propyl)-benzyloxy]-dimethyl-silane (383125-00-6) + (R)-2-((2R,3S,4S,6S,8S)-4,8-Bis-benzyloxy-2-ethyl-1,5-dioxa-spiro[2.5]oct-6-yl)-pentanal (383125-01-7) → (R)-2-((2R,3S,4S,6S,8S)-4,8-Bis-benzyloxy-2-ethyl-1,5-dioxa-spiro[2.5]oct-6-yl)-1-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,4-bis-methoxymethoxy-5-((R)-1-methoxy-2-methyl-propyl)-phenyl]-pentan-1-one (383125-20-0)

Guidance literature:

tert-butyl-[3-iodo-2,6-bis-methoxymethoxy-5-(1-methoxy-2-methyl-propyl)-benzyloxy]-dimethyl-silane; (R)-2-((2R,3S,4S,6S,8S)-4,8-Bis-benzyloxy-2-ethyl-1,5-dioxa-spiro[2.5]oct-6-yl)-pentanal; With n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃;

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(01)01657-4

Reference yield:

3,6-di-O-acetyl-D-glucal (63914-23-8) → (R)-2-((2R,3S,4S,6S,8S)-4,8-Bis-benzyloxy-2-ethyl-1,5-dioxa-spiro[2.5]oct-6-yl)-1-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,4-bis-methoxymethoxy-5-((R)-1-methoxy-2-methyl-propyl)-phenyl]-pentan-1-one (383125-20-0)

Guidance literature:

Multi-step reaction with 27 steps

1.1: i-Pr₂NEt / toluene / 20 °C

2.1: NH₃ / methanol / 40 °C

3.1: t-BuOK / dimethylformamide / 20 °C

4.1: Ph₃P*HBr / toluene / 20 °C

4.2: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0 h / -78 °C

5.1: 84 percent / n-BuLi / tetrahydrofuran / 20 h / -78 °C

6.1: 80 percent / AcOH; water / 50 °C

7.1: 76 percent / toluene / 100 °C

8.1: 80 percent / MeONa / toluene / 70 °C

9.1: 45 percent / MeONa / methanol / 60 °C

10.1: 100 percent / OsO₄; NMO / acetonitrile; H₂O / 20 °C

11.1: 100 percent / PPTS / CHCl₃ / 20 °C

12.1: 100 percent / H₂ / Pd(OH)2/C / ethanol / 20 °C

13.1: SOCl₂; Et₃N / CH₂Cl₂ / -78 °C

13.2: RuCl₃*nH₂O; NaIO₄ / CCl₄; acetonitrile; H₂O / 20 °C

14.1: tetrahydrofuran / 0 °C

14.2: H₂SO₄; water / tetrahydrofuran / 20 °C

15.1: H₂O₂; water; NaHCO₃ / tetrahydrofuran / 20 - 50 °C

16.1: TPAP; NMO; MS 4A / CH₂Cl₂ / 20 °C

17.1: LiAlH₄ / tetrahydrofuran / 0 - 20 °C

18.1: imidazole / dimethylformamide / 20 °C

19.1: 95 percent / NaH / dimethylformamide / 20 °C

20.1: 80 percent / O₃ / CH₂Cl₂ / -78 °C

21.1: 80 percent / TFA / CH₂Cl₂ / 20 °C

22.1: Tf₂O; pyridine / CH₂Cl₂ / -78 °C

23.1: DIBAL-H / toluene / -78 °C

24.1: NaH / dimethylformamide / 20 °C

25.1: TBAF / tetrahydrofuran / 20 °C

26.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

27.1: n-BuLi / tetrahydrofuran / -78 - 0 °C

27.2: 70 percent / TPAP; NMO; MS 4A / CH₂Cl₂ / 20 °C

With pyridine; 1H-imidazole; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; trifluoromethylsulfonic anhydride; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; water; hydrogen; dihydrogen peroxide; sodium methylate; triphenylphosphine hydrobromide; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile; 5.1: Wittig olefination / 7.1: Wittig reaction / 8.1: Michael reaction;

DOI:10.1016/S0040-4039(01)01657-4

Reference yield:

3,6-Di-O-acetyl-1,5-anhydro-4-O-(methoxymethyl)-2-deoxy-D-arabino-hex-1-enitol → (R)-2-((2R,3S,4S,6S,8S)-4,8-Bis-benzyloxy-2-ethyl-1,5-dioxa-spiro[2.5]oct-6-yl)-1-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,4-bis-methoxymethoxy-5-((R)-1-methoxy-2-methyl-propyl)-phenyl]-pentan-1-one (383125-20-0)

Guidance literature:

Multi-step reaction with 26 steps

1.1: NH₃ / methanol / 40 °C

2.1: t-BuOK / dimethylformamide / 20 °C

3.1: Ph₃P*HBr / toluene / 20 °C

3.2: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0 h / -78 °C

4.1: 84 percent / n-BuLi / tetrahydrofuran / 20 h / -78 °C

5.1: 80 percent / AcOH; water / 50 °C

6.1: 76 percent / toluene / 100 °C

7.1: 80 percent / MeONa / toluene / 70 °C

8.1: 45 percent / MeONa / methanol / 60 °C

9.1: 100 percent / OsO₄; NMO / acetonitrile; H₂O / 20 °C

10.1: 100 percent / PPTS / CHCl₃ / 20 °C

11.1: 100 percent / H₂ / Pd(OH)2/C / ethanol / 20 °C

12.1: SOCl₂; Et₃N / CH₂Cl₂ / -78 °C

12.2: RuCl₃*nH₂O; NaIO₄ / CCl₄; acetonitrile; H₂O / 20 °C

13.1: tetrahydrofuran / 0 °C

13.2: H₂SO₄; water / tetrahydrofuran / 20 °C

14.1: H₂O₂; water; NaHCO₃ / tetrahydrofuran / 20 - 50 °C

15.1: TPAP; NMO; MS 4A / CH₂Cl₂ / 20 °C

16.1: LiAlH₄ / tetrahydrofuran / 0 - 20 °C

17.1: imidazole / dimethylformamide / 20 °C

18.1: 95 percent / NaH / dimethylformamide / 20 °C

19.1: 80 percent / O₃ / CH₂Cl₂ / -78 °C

20.1: 80 percent / TFA / CH₂Cl₂ / 20 °C

21.1: Tf₂O; pyridine / CH₂Cl₂ / -78 °C

22.1: DIBAL-H / toluene / -78 °C

23.1: NaH / dimethylformamide / 20 °C

24.1: TBAF / tetrahydrofuran / 20 °C

25.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

26.1: n-BuLi / tetrahydrofuran / -78 - 0 °C

26.2: 70 percent / TPAP; NMO; MS 4A / CH₂Cl₂ / 20 °C

With pyridine; 1H-imidazole; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; trifluoromethylsulfonic anhydride; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; water; hydrogen; dihydrogen peroxide; sodium methylate; triphenylphosphine hydrobromide; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; acetic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile; 4.1: Wittig olefination / 6.1: Wittig reaction / 7.1: Michael reaction;

DOI:10.1016/S0040-4039(01)01657-4

upstream raw materials:

tert-butyl-[3-iodo-2,6-bis-methoxymethoxy-5-(1-methoxy-2-methyl-propyl)-benzyloxy]-dimethyl-silane

(R)-2-((2R,3S,4S,6S,8S)-4,8-Bis-benzyloxy-2-ethyl-1,5-dioxa-spiro[2.5]oct-6-yl)-pentanal

3,6-di-O-acetyl-D-glucal

2,4-bis(methoxymethoxy)benzaldehyde

Downstream raw materials:

(R)-2-((2R,3R,4S,6S,8S)-2-Ethyl-4,8-dihydroxy-1,5-dioxa-spiro[2.5]oct-6-yl)-1-[2-hydroxy-3-hydroxymethyl-4-methoxymethoxy-5-((R)-1-methoxy-2-methyl-propyl)-phenyl]-pentan-1-one