(2S,3R,6R,7S)-6-Benzyloxy-2-[(2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-7-(3-benzyloxy-propyl)-7-methyl-oxepan-3-ol

Base Information

• Chemical Name: (2S,3R,6R,7S)-6-Benzyloxy-2-[(2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-7-(3-benzyloxy-propyl)-7-methyl-oxepan-3-ol
• CAS No.: 436153-86-5
• Molecular Formula: C₅₁H₇₀O₈Si
• Molecular Weight: 839.197

Synonyms:(2S,3R,6R,7S)-6-Benzyloxy-2-[(2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-7-(3-benzyloxy-propyl)-7-methyl-oxepan-3-ol

Chemical Property of (2S,3R,6R,7S)-6-Benzyloxy-2-[(2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-7-(3-benzyloxy-propyl)-7-methyl-oxepan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,6R,7S)-6-Benzyloxy-2-[(2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-7-(3-benzyloxy-propyl)-7-methyl-oxepan-3-ol

There total 23 articles about (2S,3R,6R,7S)-6-Benzyloxy-2-[(2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-7-(3-benzyloxy-propyl)-7-methyl-oxepan-3-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:

(5R,6S)-5,9-Bis-benzyloxy-6-methoxymethoxy-6-methyl-nonanal → (2S,3R,6R,7S)-6-Benzyloxy-2-[(2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-7-(3-benzyloxy-propyl)-7-methyl-oxepan-3-ol (436153-86-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

2.1: 3.02 g / trifluoroacetic acid / CH₂Cl₂ / 0 - 20 °C

3.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 2 h / 20 °C

3.2: 62 percent / 4-(dimethylamino)pyridine / toluene / Heating

4.1: potassium hexamethyldisilazanide; hexamethylphosphortriamide / tetrahydrofuran; toluene / 0.5 h / -78 °C

5.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C

5.2: Cs₂CO₃ / PdCl₂(dppf)*CH₂Cl₂ / dimethylformamide; H₂O / 16 h / 50 °C

5.3: 86 percent / aq. NAOH; H₂O₂ / tetrahydrofuran / 0 - 20 °C

6.1: BH₃*THF / tetrahydrofuran / 0 °C

6.2: 37 percent / sodium hydroxide; hydrogen peroxide / H₂O; tetrahydrofuran / 0.5 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; borane-THF; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; potassium hexamethylsilazane; triethylamine; 9-bora-bicyclo[3.3.1]nonane; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; 5.2: Suzuki-Miyaura coupling;

DOI:10.1021/ol025814u

Reference yield:

benzyl bromide (100-39-0) → (2S,3R,6R,7S)-6-Benzyloxy-2-[(2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-7-(3-benzyloxy-propyl)-7-methyl-oxepan-3-ol (436153-86-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: KOt-Bu / tetrahydrofuran / 1 h / 20 °C

2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 5 h / 20 °C

3.1: sodium periodate / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 1 h / 20 °C

4.1: 8.39 g / sodium borohydride / methanol / 0.33 h / 0 °C

5.1: 81 percent / iodide; triphenylphosphane; imidazole / benzene / 0.5 h / 20 °C

6.1: 100 percent / KOt-Bu / tetrahydrofuran / 2 h / 0 °C

7.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C

7.2: Cs₂CO₃ / PdCl₂(dppf)*CH₂Cl₂ / dimethylformamide; H₂O / 16 h / 50 °C

7.3: 86 percent / aq. NAOH; H₂O₂ / tetrahydrofuran / 0 - 20 °C

8.1: BH₃*THF / tetrahydrofuran / 0 °C

8.2: 37 percent / sodium hydroxide; hydrogen peroxide / H₂O; tetrahydrofuran / 0.5 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; borane-THF; potassium tert-butylate; iodide; 4-methylmorpholine N-oxide; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; In tetrahydrofuran; methanol; water; tert-butyl alcohol; benzene; 7.2: Suzuki-Miyaura coupling;

DOI:10.1021/ol025814u

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3R,6R,7S)-6-Benzyloxy-2-[(2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-7-(3-benzyloxy-propyl)-7-methyl-oxepan-3-ol (436153-86-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 81 percent / imidazole / dimethylformamide / 20 °C

2.1: 99 percent / EtSH; Zn(OTf)2; NaHCO₃ / CH₂Cl₂ / 8.5 h / 20 °C

3.1: KOt-Bu / tetrahydrofuran / 1 h / 20 °C

4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 5 h / 20 °C

5.1: sodium periodate / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 1 h / 20 °C

6.1: 8.39 g / sodium borohydride / methanol / 0.33 h / 0 °C

7.1: 81 percent / iodide; triphenylphosphane; imidazole / benzene / 0.5 h / 20 °C

8.1: 100 percent / KOt-Bu / tetrahydrofuran / 2 h / 0 °C

9.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C

9.2: Cs₂CO₃ / PdCl₂(dppf)*CH₂Cl₂ / dimethylformamide; H₂O / 16 h / 50 °C

9.3: 86 percent / aq. NAOH; H₂O₂ / tetrahydrofuran / 0 - 20 °C

10.1: BH₃*THF / tetrahydrofuran / 0 °C

10.2: 37 percent / sodium hydroxide; hydrogen peroxide / H₂O; tetrahydrofuran / 0.5 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; borane-THF; potassium tert-butylate; iodide; zinc trifluoromethanesulfonate; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; ethanethiol; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 9.2: Suzuki-Miyaura coupling;

DOI:10.1021/ol025814u

upstream raw materials:

benzyl bromide

tert-butyldimethylsilyl chloride

(2R,4aR,6S,7R,8aS)-2-Phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

(2R,3S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-6-vinyl-tetrahydro-pyran-3-ol

Downstream raw materials:

(2S,6R,7S)-6-Benzyloxy-2-[(2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-7-(3-benzyloxy-propyl)-7-methyl-oxepan-3-one

(4aR,5aS,6aR,8S,9R,11aS,12aR,13aS)-8-(3-Hydroxy-propyl)-2-(4-methoxy-phenyl)-8-methyl-dodecahydro-1,3,5,7,12-pentaoxa-cyclohepta[b]anthracen-9-ol

(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2,9-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-ol

[(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2,9-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy]-tert-butyl-dimethyl-silane

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