5-isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-1,2,7,7a-tetrahydro-5H-pyrano[3,4-b]pyrrol-3-one

Base Information

• Chemical Name: 5-isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-1,2,7,7a-tetrahydro-5H-pyrano[3,4-b]pyrrol-3-one
• CAS No.: 871483-75-9
• Molecular Formula: C₂₈H₄₅NO₆SSi
• Molecular Weight: 551.82

Synonyms:5-isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-1,2,7,7a-tetrahydro-5H-pyrano[3,4-b]pyrrol-3-one

Chemical Property of 5-isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-1,2,7,7a-tetrahydro-5H-pyrano[3,4-b]pyrrol-3-one

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of 5-isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-1,2,7,7a-tetrahydro-5H-pyrano[3,4-b]pyrrol-3-one

There total 8 articles about 5-isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-1,2,7,7a-tetrahydro-5H-pyrano[3,4-b]pyrrol-3-one 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: 72.0%

2-[(4-iodo-6-isobutoxy-2-triisopropylsilanyloxymethyl-3,6-dihydro-2H-pyran-3-yl)-(toluene-4-sulfonyl)-amino]-N-methoxy-N-methyl-acetamide (871483-63-5) → 5-isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-1,2,7,7a-tetrahydro-5H-pyrano[3,4-b]pyrrol-3-one (871483-75-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/j.bmcl.2005.08.062

Reference yield:

(2R,3S)-2-Hydroxymethyl-6-isobutoxy-3,6-dihydro-2H-pyran-3-ol → 5-isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-1,2,7,7a-tetrahydro-5H-pyrano[3,4-b]pyrrol-3-one (871483-75-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 2,6-lutidine / -5 °C

2: 96 percent / (COCl)2; DMSO; Et₃N / -78 °C

3: 96 percent / I₂; pyridine / CH₂Cl₂

4: 67 percent / NaBH₄; CeCl₃*7H₂O / methanol

5: 57 percent / DIAD; PPh₃ / tetrahydrofuran / 20 °C

6: 72 percent / n-BuLi / tetrahydrofuran / -78 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; oxalyl dichloride; di-isopropyl azodicarboxylate; iodine; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 2: Swern oxidation / 4: Luche reduction / 5: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2005.08.062

Reference yield:

Acetic acid (2R,3S)-2-acetoxymethyl-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl ester → 5-isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-1,2,7,7a-tetrahydro-5H-pyrano[3,4-b]pyrrol-3-one (871483-75-9)

Guidance literature:

Multi-step reaction with 7 steps

1: K₂CO₃; MeOH

2: 2,6-lutidine / -5 °C

3: 96 percent / (COCl)2; DMSO; Et₃N / -78 °C

4: 96 percent / I₂; pyridine / CH₂Cl₂

5: 67 percent / NaBH₄; CeCl₃*7H₂O / methanol

6: 57 percent / DIAD; PPh₃ / tetrahydrofuran / 20 °C

7: 72 percent / n-BuLi / tetrahydrofuran / -78 °C

With pyridine; 2,6-dimethylpyridine; methanol; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; oxalyl dichloride; di-isopropyl azodicarboxylate; iodine; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 3: Swern oxidation / 5: Luche reduction / 6: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2005.08.062

upstream raw materials:

2-[(4-iodo-6-isobutoxy-2-triisopropylsilanyloxymethyl-3,6-dihydro-2H-pyran-3-yl)-(toluene-4-sulfonyl)-amino]-N-methoxy-N-methyl-acetamide

(2R,3S,6S)-6-Isobutoxy-2-triisopropylsilanyloxymethyl-3,6-dihydro-2H-pyran-3-ol

(2R,6S)-6-Isobutoxy-2-triisopropylsilanyloxymethyl-6H-pyran-3-one

(2R,6S)-4-Iodo-6-isobutoxy-2-triisopropylsilanyloxymethyl-6H-pyran-3-one

Downstream raw materials:

(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[(3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-(3-phenyl-propionyloxymethyl)-hexahydro-pyrano[3,4-b]pyrrol-1-yl]-acetylamino}-succinamic acid benzyl ester

(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-[2-((3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-triisopropylsilanyloxymethyl-hexahydro-pyrano[3,4-b]pyrrol-1-yl)-acetylamino]-succinamic acid benzyl ester

(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-[2-((3S,3aR,5S,7S,7aS)-3-benzyloxy-7-hydroxymethyl-5-isobutoxy-hexahydro-pyrano[3,4-b]pyrrol-1-yl)-acetylamino]-succinamic acid benzyl ester

(3S,3aR,5S,7S,7aS)-3-Benzyloxy-5-isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-octahydro-pyrano[3,4-b]pyrrole

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