(3S,4S,5S)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-3-hydroxy-4-(2-methoxyethoxymethoxy)-5-(phenylmethoxymethyl)hexyl 2,2-dimethylpropanoate

Base Information

• Chemical Name: (3S,4S,5S)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-3-hydroxy-4-(2-methoxyethoxymethoxy)-5-(phenylmethoxymethyl)hexyl 2,2-dimethylpropanoate
• CAS No.: 667422-02-8
• Molecular Formula: C₅₀H₇₈O₁₀Si₂
• Molecular Weight: 895.334

Synonyms:(3S,4S,5S)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-3-hydroxy-4-(2-methoxyethoxymethoxy)-5-(phenylmethoxymethyl)hexyl 2,2-dimethylpropanoate

Chemical Property of (3S,4S,5S)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-3-hydroxy-4-(2-methoxyethoxymethoxy)-5-(phenylmethoxymethyl)hexyl 2,2-dimethylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5S)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-3-hydroxy-4-(2-methoxyethoxymethoxy)-5-(phenylmethoxymethyl)hexyl 2,2-dimethylpropanoate

There total 24 articles about (3S,4S,5S)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-3-hydroxy-4-(2-methoxyethoxymethoxy)-5-(phenylmethoxymethyl)hexyl 2,2-dimethylpropanoate 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: 88.0%

pivaloyl chloride (3282-30-2) + (3S,4S,5S)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-4-(2-methoxyethoxymethoxy)-5-(phenylmethoxymethyl)hexane-1,3-diol (667422-01-7) → (3S,4S,5S)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-3-hydroxy-4-(2-methoxyethoxymethoxy)-5-(phenylmethoxymethyl)hexyl 2,2-dimethylpropanoate (667422-02-8)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 6h;

DOI:10.3987/com-03-9952

Reference yield:

methyl (3S)-4-tert-butyldiphenylsiloxy-3-triethylsiloxybutanoate (667421-82-1) → (3S,4S,5S)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-3-hydroxy-4-(2-methoxyethoxymethoxy)-5-(phenylmethoxymethyl)hexyl 2,2-dimethylpropanoate (667422-02-8)

Guidance literature:

Multi-step reaction with 19 steps

1.1: DIBAL-H / toluene / 1 h / -78 °C

1.2: 94 percent / benzene / 8 h / 20 °C

2.1: 95 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

3.1: 90 percent / Ti(Oi-Pr)4; (-)-diethyl-D-tartrate; TBHP / CH₂Cl₂; 2,2,4-trimethyl-pentane / 5 h / -20 °C

4.1: DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C

4.2: 79 percent / benzene / 8 h / 20 °C

5.1: 82 percent / CSA / methanol / 0.08 h / 0 °C

6.1: 90 percent / Ph₃P; Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 0.08 h / 20 °C

7.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

8.1: hydrogen / Pd-C / ethanol / 2 h / 20 °C

9.1: 8.82 g / LiOH*H₂O / H₂O; methanol; tetrahydrofuran / 2 h / 20 °C

10.1: PivCl; Et₃N / tetrahydrofuran / 0.75 h / 0 °C

10.2: 88 percent / LiCl / tetrahydrofuran / 2 h / 20 °C

11.1: LHMDS / tetrahydrofuran / 0.75 h / -78 °C

11.2: 78 percent / LiI / tetrahydrofuran / 1 h / -50 °C

12.1: 91 percent / LiBH₄ / ethanol; tetrahydrofuran; H₂O / 2 h / 0 °C

13.1: tetra-n-propylammonium perruthenate; NMO; MS₄Angstroem / CH₂Cl₂

14.1: LMHDS / tetrahydrofuran / 1 h / -78 °C

14.2: 0.93 g / -78 °C

15.1: 95 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 48 h / 20 °C

16.1: 61 percent / MS₄Angstroem; DDQ / CH₂Cl₂ / 0.25 h / 20 °C

17.1: 91 percent / iPr₂NEt / CH₂Cl₂ / 40 h / Heating

18.1: 91 percent / aq. AcOH / 1 h / 20 °C

19.1: 88 percent / pyridine / CH₂Cl₂ / 6 h / 20 °C

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; lithium hydroxide; AD-mix-α; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; methanesulfonamide; MS₄Angstroem; camphor-10-sulfonic acid; hydrogen; pivaloyl chloride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; ethanol; dichloromethane; water; toluene; tert-butyl alcohol; 1.2: Wittig reaction / 3.1: Sharpless asymmetric epoxydation / 4.2: Wittig reaction / 14.2: Julia olefination / 15.1: Sharpless asymmetric dihydroxylation;

DOI:10.3987/com-03-9952

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (3S,4S,5S)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-3-hydroxy-4-(2-methoxyethoxymethoxy)-5-(phenylmethoxymethyl)hexyl 2,2-dimethylpropanoate (667422-02-8)

Guidance literature:

Multi-step reaction with 20 steps

1.1: imidazole / dimethylformamide / 0.33 h / 20 °C

1.2: 95 percent / imidazole / dimethylformamide / 0.33 h / 0 °C

2.1: DIBAL-H / toluene / 1 h / -78 °C

2.2: 94 percent / benzene / 8 h / 20 °C

3.1: 95 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

4.1: 90 percent / Ti(Oi-Pr)4; (-)-diethyl-D-tartrate; TBHP / CH₂Cl₂; 2,2,4-trimethyl-pentane / 5 h / -20 °C

5.1: DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C

5.2: 79 percent / benzene / 8 h / 20 °C

6.1: 82 percent / CSA / methanol / 0.08 h / 0 °C

7.1: 90 percent / Ph₃P; Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 0.08 h / 20 °C

8.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

9.1: hydrogen / Pd-C / ethanol / 2 h / 20 °C

10.1: 8.82 g / LiOH*H₂O / H₂O; methanol; tetrahydrofuran / 2 h / 20 °C

11.1: PivCl; Et₃N / tetrahydrofuran / 0.75 h / 0 °C

11.2: 88 percent / LiCl / tetrahydrofuran / 2 h / 20 °C

12.1: LHMDS / tetrahydrofuran / 0.75 h / -78 °C

12.2: 78 percent / LiI / tetrahydrofuran / 1 h / -50 °C

13.1: 91 percent / LiBH₄ / ethanol; tetrahydrofuran; H₂O / 2 h / 0 °C

14.1: tetra-n-propylammonium perruthenate; NMO; MS₄Angstroem / CH₂Cl₂

15.1: LMHDS / tetrahydrofuran / 1 h / -78 °C

15.2: 0.93 g / -78 °C

16.1: 95 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 48 h / 20 °C

17.1: 61 percent / MS₄Angstroem; DDQ / CH₂Cl₂ / 0.25 h / 20 °C

18.1: 91 percent / iPr₂NEt / CH₂Cl₂ / 40 h / Heating

19.1: 91 percent / aq. AcOH / 1 h / 20 °C

20.1: 88 percent / pyridine / CH₂Cl₂ / 6 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; lithium hydroxide; AD-mix-α; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; methanesulfonamide; MS₄Angstroem; camphor-10-sulfonic acid; hydrogen; pivaloyl chloride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 2.2: Wittig reaction / 4.1: Sharpless asymmetric epoxydation / 5.2: Wittig reaction / 15.2: Julia olefination / 16.1: Sharpless asymmetric dihydroxylation;

DOI:10.3987/com-03-9952

upstream raw materials:

pivaloyl chloride

(3S,4S,5S)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-4-(2-methoxyethoxymethoxy)-5-(phenylmethoxymethyl)hexane-1,3-diol

Benzyloxymethyl chloride

t-butyldimethylsiyl triflate

Downstream raw materials:

(3S,4S,5S)-5-{[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]methyl}-3,6-dihydroxy-4-(2-methoxyethoxymethoxy)hexyl 2,2-dimethylpropanoate

{(1S,3R,5S,7R,9R,12R)-2,6,15-trioxa-11-thiatetracyclo[7.6.0.0^1,12.0^3,7]pentadec-5-yl}tert-butyldiphenylsiloxymethane

2-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.0^3,7]dodec-4-yl]ethan-1-ol

(2R,3S,4R)-2-{4-[[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]methyl]-3-hydroxythiolan-2-yl}ethyl 2,2-dimethylpropanoate

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