(1S,2S)-1-[(4S)-2-(4-methoxyphenyl)1,3-dioxan-4-yl]-3-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-2-phenylmethoxymethylpropan-1-ol

Base Information

• Chemical Name: (1S,2S)-1-[(4S)-2-(4-methoxyphenyl)1,3-dioxan-4-yl]-3-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-2-phenylmethoxymethylpropan-1-ol
• CAS No.: 667422-00-6
• Molecular Formula: C₄₉H₆₈O₈Si₂
• Molecular Weight: 841.245

Synonyms:(1S,2S)-1-[(4S)-2-(4-methoxyphenyl)1,3-dioxan-4-yl]-3-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-2-phenylmethoxymethylpropan-1-ol

Chemical Property of (1S,2S)-1-[(4S)-2-(4-methoxyphenyl)1,3-dioxan-4-yl]-3-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-2-phenylmethoxymethylpropan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (1S,2S)-1-[(4S)-2-(4-methoxyphenyl)1,3-dioxan-4-yl]-3-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-2-phenylmethoxymethylpropan-1-ol

There total 19 articles about (1S,2S)-1-[(4S)-2-(4-methoxyphenyl)1,3-dioxan-4-yl]-3-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-2-phenylmethoxymethylpropan-1-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: 61.0%

(2S,3S,4S)-1-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-6-(4-methoxyphenylmethoxy)-2-phenylmethoxymethylhexane-3,4-diol (667421-92-3) → (1S,2S)-1-[(4S)-2-(4-methoxyphenyl)1,3-dioxan-4-yl]-3-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-2-phenylmethoxymethylpropan-1-ol (667422-00-6)

Guidance literature:

With MS₄Angstroem; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.3987/com-03-9952

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (1S,2S)-1-[(4S)-2-(4-methoxyphenyl)1,3-dioxan-4-yl]-3-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-2-phenylmethoxymethylpropan-1-ol (667422-00-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

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

3.1: 8.82 g / LiOH*H₂O / H₂O; methanol; tetrahydrofuran / 2 h / 20 °C

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

4.2: 88 percent / LiCl / tetrahydrofuran / 2 h / 20 °C

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

5.2: 78 percent / LiI / tetrahydrofuran / 1 h / -50 °C

6.1: 91 percent / LiBH₄ / ethanol; tetrahydrofuran; H₂O / 2 h / 0 °C

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

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

8.2: 0.93 g / -78 °C

9.1: 95 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 48 h / 20 °C

10.1: 61 percent / MS₄Angstroem; DDQ / CH₂Cl₂ / 0.25 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; AD-mix-α; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; methanesulfonamide; MS₄Angstroem; hydrogen; pivaloyl chloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; tert-butyl alcohol; 8.2: Julia olefination / 9.1: Sharpless asymmetric dihydroxylation;

DOI:10.3987/com-03-9952

Reference yield:

methyl (3S)-4-tert-butyldiphenylsiloxy-3-triethylsiloxybutanoate (667421-82-1) → (1S,2S)-1-[(4S)-2-(4-methoxyphenyl)1,3-dioxan-4-yl]-3-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-2-phenylmethoxymethylpropan-1-ol (667422-00-6)

Guidance literature:

Multi-step reaction with 16 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

With 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; dimethyl sulfoxide; triethylamine; 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

upstream raw materials:

(2S,3S,4S)-1-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-6-(4-methoxyphenylmethoxy)-2-phenylmethoxymethylhexane-3,4-diol

Benzyloxymethyl chloride

t-butyldimethylsiyl triflate

methyl (3S)-4-tert-butyldiphenylsiloxy-3-triethylsiloxybutanoate

Downstream raw materials:

{(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

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

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