3-[(2R,3S,4aR,8aS)-3-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propionic acid (2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 3-[(2R,3S,4aR,8aS)-3-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propionic acid (2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 856426-91-0
• Molecular Formula: C₃₄H₅₆O₇Si
• Molecular Weight: 604.9
• Mol file: 856426-91-0.mol

Synonyms:3-[(2R,3S,4aR,8aS)-3-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propionic acid (2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yl ester

Chemical Property of 3-[(2R,3S,4aR,8aS)-3-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propionic acid (2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of 3-[(2R,3S,4aR,8aS)-3-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propionic acid (2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yl ester

There total 21 articles about 3-[(2R,3S,4aR,8aS)-3-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propionic acid (2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yl ester 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: 100.0%

(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-ol (856426-83-0) + 3-[(2R,3S,4aR,8aS)-3-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propionic acid (856426-84-1) → 3-[(2R,3S,4aR,8aS)-3-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propionic acid (2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yl ester (856426-91-0)

Guidance literature:

With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/ol050760k

Reference yield:

1-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propan-2-ol → 3-[(2R,3S,4aR,8aS)-3-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propionic acid (2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yl ester (856426-91-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 2.89 g / tetra-n-propylammonium perruthenate; NMO; molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / 0 - 20 °C

2.1: 94 percent / TBAF / tetrahydrofuran / 14 h / 20 °C

3.1: 87 percent / 4-methylmorpholine / CH₂Cl₂ / 14 h / 20 °C

4.1: 99 percent / SmI₂ / tetrahydrofuran; methanol / 0.25 h / 0 °C

5.1: 2,6-lutidine / CH₂Cl₂ / 13 h / 0 - 20 °C

6.1: DIBALH / CH₂Cl₂; hexane / 1.5 h / -78 °C

7.1: NaHMDS / CH₂Cl₂; tetrahydrofuran / 0.5 h / 0 °C

7.2: 0.61 g / tetrahydrofuran; CH₂Cl₂ / 9 h / 20 °C

8.1: 9-BBN-H / tetrahydrofuran / 4 h / 20 °C

8.2: 1.74 g / H₂O₂; aq. NaOH / tetrahydrofuran / 12 h / 20 °C

9.1: Et₃N; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 4 h / 20 °C

10.1: 1.75 g / NaClO₂; 2-methyl-2-butene; KH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

11.1: Et₃N / tetrahydrofuran / 1.5 h / 20 °C

12.1: 0.85 g / DMAP / tetrahydrofuran / 2 h / 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; dmap; sodium chlorite; potassium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; pyridine-SO₃ complex; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; 7.2: Wittig reaction / 9.1: Parikh-Doering oxidation;

DOI:10.1016/j.tet.2007.02.039

Reference yield:

1-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propan-2-one (856426-89-6) → 3-[(2R,3S,4aR,8aS)-3-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propionic acid (2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yl ester (856426-91-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 94 percent / TBAF / tetrahydrofuran / 14 h / 20 °C

2.1: 87 percent / 4-methylmorpholine / CH₂Cl₂ / 14 h / 20 °C

3.1: 99 percent / SmI₂ / tetrahydrofuran; methanol / 0.25 h / 0 °C

4.1: 2,6-lutidine / CH₂Cl₂ / 13 h / 0 - 20 °C

5.1: DIBALH / CH₂Cl₂; hexane / 1.5 h / -78 °C

6.1: NaHMDS / CH₂Cl₂; tetrahydrofuran / 0.5 h / 0 °C

6.2: 0.61 g / tetrahydrofuran; CH₂Cl₂ / 9 h / 20 °C

7.1: 9-BBN-H / tetrahydrofuran / 4 h / 20 °C

7.2: 1.74 g / H₂O₂; aq. NaOH / tetrahydrofuran / 12 h / 20 °C

8.1: Et₃N; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 4 h / 20 °C

9.1: 1.75 g / NaClO₂; 2-methyl-2-butene; KH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

10.1: Et₃N / tetrahydrofuran / 1.5 h / 20 °C

11.1: 0.85 g / DMAP / tetrahydrofuran / 2 h / 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; dmap; sodium chlorite; potassium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; samarium diiodide; 2-methyl-but-2-ene; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; 6.2: Wittig reaction / 8.1: Parikh-Doering oxidation;

DOI:10.1016/j.tet.2007.02.039

upstream raw materials:

(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-ol

3-[(2R,3S,4aR,8aS)-3-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propionic acid

1-((2R,3S)-3-Hydroxy-tetrahydro-pyran-2-yl)-propan-2-one

1-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propan-2-one

Downstream raw materials:

((2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-tert-butyl-dimethyl-silane

(E)-3-((2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-acrylic acid methyl ester

Acetic acid 1-[(2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-[(2R,3S,4aR,8aS)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propyl ester

(2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-ol