[(2E,9Z)-(1S,4S,7R)-10-[(2R,5S,6R)-6-(3-benzyloxypropyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-7-(4-methoxybenzyloxy)-1,2,4-trimethyl-deca-2,9-dienyloxy](tert-butyl)(dimethyl)silane

Base Information

• Chemical Name: [(2E,9Z)-(1S,4S,7R)-10-[(2R,5S,6R)-6-(3-benzyloxypropyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-7-(4-methoxybenzyloxy)-1,2,4-trimethyl-deca-2,9-dienyloxy](tert-butyl)(dimethyl)silane
• CAS No.: 927396-47-2
• Molecular Formula: C₄₄H₇₀O₆Si
• Molecular Weight: 723.122

Synonyms:[(2E,9Z)-(1S,4S,7R)-10-[(2R,5S,6R)-6-(3-benzyloxypropyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-7-(4-methoxybenzyloxy)-1,2,4-trimethyl-deca-2,9-dienyloxy](tert-butyl)(dimethyl)silane

Chemical Property of [(2E,9Z)-(1S,4S,7R)-10-[(2R,5S,6R)-6-(3-benzyloxypropyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-7-(4-methoxybenzyloxy)-1,2,4-trimethyl-deca-2,9-dienyloxy](tert-butyl)(dimethyl)silane

Chemical Property:

Purity/Quality:

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Technology Process of [(2E,9Z)-(1S,4S,7R)-10-[(2R,5S,6R)-6-(3-benzyloxypropyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-7-(4-methoxybenzyloxy)-1,2,4-trimethyl-deca-2,9-dienyloxy](tert-butyl)(dimethyl)silane

There total 14 articles about [(2E,9Z)-(1S,4S,7R)-10-[(2R,5S,6R)-6-(3-benzyloxypropyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-7-(4-methoxybenzyloxy)-1,2,4-trimethyl-deca-2,9-dienyloxy](tert-butyl)(dimethyl)silane 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: 86.0%

(2R,5S,6R)-6-(3-benzyloxy-propyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-carbaldehyde (927396-36-9) + [(E)-(3R,6S,9S)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-dec-7-enyl]-triphenyl-phosphonium bromide → [(2E,9Z)-(1S,4S,7R)-10-[(2R,5S,6R)-6-(3-benzyloxypropyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-7-(4-methoxybenzyloxy)-1,2,4-trimethyl-deca-2,9-dienyloxy](tert-butyl)(dimethyl)silane (927396-47-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

DOI:10.1021/ol062957y

Reference yield:

4-benzyloxybutanal (5470-84-8) → [(2E,9Z)-(1S,4S,7R)-10-[(2R,5S,6R)-6-(3-benzyloxypropyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-7-(4-methoxybenzyloxy)-1,2,4-trimethyl-deca-2,9-dienyloxy](tert-butyl)(dimethyl)silane (927396-47-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / -50 °C

2: 96 percent / tetra-n-butylammonium hydroxide / tetrahydrofuran; methanol / 1 h / 20 °C

3: 81 percent / 10-camphorsulfonic acid / 120 h / 60 °C

4: 94 percent / diisobutylaluminum hydride / hexane; diethyl ether / 4.5 h / -78 °C

5: 86 percent / n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C

With n-butyllithium; trimethylsilyl trifluoromethanesulfonate; (1S)-10-camphorsulfonic acid; tetra(n-butyl)ammonium hydroxide; diisobutylaluminium hydride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; 5: Wittig olefination;

DOI:10.1021/ol062957y

Reference yield:

(S)-4-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-2-methylbutyraldehyde (927396-58-5) → [(2E,9Z)-(1S,4S,7R)-10-[(2R,5S,6R)-6-(3-benzyloxypropyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-7-(4-methoxybenzyloxy)-1,2,4-trimethyl-deca-2,9-dienyloxy](tert-butyl)(dimethyl)silane (927396-47-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 0.750 g / Ba(OH)2 / tetrahydrofuran; H₂O / 0.5 h / 20 °C

2: (R)-CBS; catecholborane / toluene / 12 h / -78 °C

3: 86 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

4: 98 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.5 h / 0 °C

5: 97 percent / triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 1 h / 20 °C

6: 96 percent / N,N-diisopropylethylamine / acetonitrile / 36 h / 85 °C

7: 86 percent / n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C

With 2,6-dimethylpyridine; barium dihydroxide; n-butyllithium; carbon tetrabromide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; (R)-(+)-2-methyl-CBS-oxazaborolidine; benzo[1,3,2]dioxaborole; In tetrahydrofuran; hexane; dichloromethane; water; toluene; acetonitrile; 7: Wittig olefination;

DOI:10.1021/ol062957y

upstream raw materials:

(2R,5S,6R)-6-(3-benzyloxy-propyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-carbaldehyde

(S)-4-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-2-methylbutyraldehyde

(S)-4-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-2-methylbutan-1-ol

(2R,5S,6R)-6-(3-benzyloxy-propyl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester

Downstream raw materials:

bistramide A

{(E)-(1S,4S)-6-[(2S,6S,8R,9S)-8-(3-benzyloxy-propyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-1,2,4-trimethyl-hex-2-enyloxy}-tert-butyl-dimethyl-silane

[(E)-(1S,4S,7S)-10-[(2S,5S,6R)-6-(3-benzyloxypropyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-7-(4-methoxy-benzyloxy)-1,2,4-trimethyl-dec-2-enyloxy](tert-butyl)(dimethyl)silane

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