(R)-3-[(2R,4aR,6R,7S,8aR,9aS,10aS)-6-(tert-Butyl-dimethyl-silanyloxy)-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-2-methyl-propionic acid

Base Information

• Chemical Name: (R)-3-[(2R,4aR,6R,7S,8aR,9aS,10aS)-6-(tert-Butyl-dimethyl-silanyloxy)-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-2-methyl-propionic acid
• CAS No.: 858346-19-7
• Molecular Formula: C₂₇H₄₂O₇Si
• Molecular Weight: 506.712

Synonyms:(R)-3-[(2R,4aR,6R,7S,8aR,9aS,10aS)-6-(tert-Butyl-dimethyl-silanyloxy)-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-2-methyl-propionic acid

Chemical Property of (R)-3-[(2R,4aR,6R,7S,8aR,9aS,10aS)-6-(tert-Butyl-dimethyl-silanyloxy)-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-2-methyl-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (R)-3-[(2R,4aR,6R,7S,8aR,9aS,10aS)-6-(tert-Butyl-dimethyl-silanyloxy)-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-2-methyl-propionic acid

There total 12 articles about (R)-3-[(2R,4aR,6R,7S,8aR,9aS,10aS)-6-(tert-Butyl-dimethyl-silanyloxy)-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-2-methyl-propionic acid 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: 96.0%

(R)-3-[(2R,4aR,6R,7S,8aR,9aS,10aS)-6-(tert-Butyl-dimethyl-silanyloxy)-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-2-methyl-propionaldehyde (858346-54-0) → (R)-3-[(2R,4aR,6R,7S,8aR,9aS,10aS)-6-(tert-Butyl-dimethyl-silanyloxy)-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-2-methyl-propionic acid (858346-19-7)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; tert-butyl alcohol; at 20 ℃; for 1h;

DOI:10.1021/ja051171c

Reference yield:

(2S,3R)-3-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl]-2-methyl-oxirane-2-carbaldehyde (131310-58-2) → (R)-3-[(2R,4aR,6R,7S,8aR,9aS,10aS)-6-(tert-Butyl-dimethyl-silanyloxy)-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-2-methyl-propionic acid (858346-19-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 100 percent / benzene / 20 °C

2.1: 100 percent / TBAF / tetrahydrofuran / 20 °C

3.1: 92 percent / PPTS / CH₂Cl₂ / 0 - 20 °C

4.1: 95 percent / H₂ / Pd/C / methanol / 20 °C

5.1: 100 percent / PPTS / benzene / Heating

6.1: 94 percent / DMPU; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

7.1: Zn-Cu; DMA / benzene / 1 h / Heating

7.2: 85 percent / PdCl₂(o-Tol₃P)2 / benzene / 13 h / 40 °C

8.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 20 °C

8.2: aq. NaOH; H₂O₂ / tetrahydrofuran / 1 h / 20 °C

9.1: 76 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / 20 °C

10.1: 56 percent / aq. AcOH / tetrahydrofuran / 3 h / 20 °C

11.1: 100 percent / SO₃*pyr; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / 0 °C

12.1: 96 percent / 2-methyl-2-butene; NaH₂PO₄; aq. NaClO₂ / tetrahydrofuran; 2-methyl-propan-2-ol / 1 h / 20 °C

With 2,6-dimethylpyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; pyridine-SO₃ complex; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; 2,4-dichlorophenoxyacetic acid dimethylamine; copper; acetic acid; dimethyl sulfoxide; triethylamine; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene; tert-butyl alcohol; benzene; 1.1: Wittig reaction;

DOI:10.1021/ja051171c

Reference yield:

(E)-3-[(2R,3R)-3-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-ylmethyl)-2-methyl-oxiranyl]-acrylic acid methyl ester (350045-95-3) → (R)-3-[(2R,4aR,6R,7S,8aR,9aS,10aS)-6-(tert-Butyl-dimethyl-silanyloxy)-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-2-methyl-propionic acid (858346-19-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 92 percent / PPTS / CH₂Cl₂ / 0 - 20 °C

2.1: 95 percent / H₂ / Pd/C / methanol / 20 °C

3.1: 100 percent / PPTS / benzene / Heating

4.1: 94 percent / DMPU; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

5.1: Zn-Cu; DMA / benzene / 1 h / Heating

5.2: 85 percent / PdCl₂(o-Tol₃P)2 / benzene / 13 h / 40 °C

6.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 20 °C

6.2: aq. NaOH; H₂O₂ / tetrahydrofuran / 1 h / 20 °C

7.1: 76 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / 20 °C

8.1: 56 percent / aq. AcOH / tetrahydrofuran / 3 h / 20 °C

9.1: 100 percent / SO₃*pyr; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / 0 °C

10.1: 96 percent / 2-methyl-2-butene; NaH₂PO₄; aq. NaClO₂ / tetrahydrofuran; 2-methyl-propan-2-ol / 1 h / 20 °C

With 2,6-dimethylpyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; pyridine-SO₃ complex; dimethylsulfide borane complex; hydrogen; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; 2,4-dichlorophenoxyacetic acid dimethylamine; copper; acetic acid; dimethyl sulfoxide; triethylamine; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene; tert-butyl alcohol; benzene;

DOI:10.1021/ja051171c

upstream raw materials:

(R)-3-[(2R,4aR,6R,7S,8aR,9aS,10aS)-6-(tert-Butyl-dimethyl-silanyloxy)-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-2-methyl-propionaldehyde

(2R,4aR,8aR,9aS,10aS)-10a-Methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-one

(R)-2-Methyl-3-((2R,4aR,8aR,9aS,10aS)-10a-methyl-2-phenyl-4a,5,8a,9,9a,10a-hexahydro-4H-1,3,8,10-tetraoxa-anthracen-7-yl)-propionic acid methyl ester

Trifluoro-methanesulfonic acid (2R,4aR,8aR,9aS,10aS)-10a-methyl-2-phenyl-4a,5,8a,9,9a,10a-hexahydro-4H-1,3,8,10-tetraoxa-anthracen-7-yl ester

Downstream raw materials:

3-[6-(tert-butyl-dimethyl-silanyloxy)-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-2-methyl-propionic acid 7-benzyloxy-6-(2-benzyloxy-ethyl)-2,6,8a-trimethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-yl ester

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