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

Base Information

Chemical Name:2-[(4-iodo-6-isobutoxy-2-triisopropylsilanyloxymethyl-3,6-dihydro-2H-pyran-3-yl)-(toluene-4-sulfonyl)-amino]-N-methoxy-N-methyl-acetamide
CAS No.:871483-63-5
Molecular Formula:C₃₀H₅₁IN₂O₇SSi
Molecular Weight:738.8
Hs Code.:

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

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

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

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

There total 7 articles about 2-[(4-iodo-6-isobutoxy-2-triisopropylsilanyloxymethyl-3,6-dihydro-2H-pyran-3-yl)-(toluene-4-sulfonyl)-amino]-N-methoxy-N-methyl-acetamide 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: 57.0%

: 871483-71-5
(2R,3S,6S)-4-Iodo-6-isobutoxy-2-triisopropylsilanyloxymethyl-3,6-dihydro-2H-pyran-3-ol

: 244168-28-3
4-methylphenylsulfonamido-N-methoxy-N-methylacetamide

: 871483-63-5
2-[(4-iodo-6-isobutoxy-2-triisopropylsilanyloxymethyl-3,6-dihydro-2H-pyran-3-yl)-(toluene-4-sulfonyl)-amino]-N-methoxy-N-methyl-acetamide

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/j.bmcl.2005.08.062

Reference yield:

: (2R,3S)-2-Hydroxymethyl-6-isobutoxy-3,6-dihydro-2H-pyran-3-ol

: 871483-63-5
2-[(4-iodo-6-isobutoxy-2-triisopropylsilanyloxymethyl-3,6-dihydro-2H-pyran-3-yl)-(toluene-4-sulfonyl)-amino]-N-methoxy-N-methyl-acetamide

Guidance literature:: Multi-step reaction with 5 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

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; 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

: 871483-63-5
2-[(4-iodo-6-isobutoxy-2-triisopropylsilanyloxymethyl-3,6-dihydro-2H-pyran-3-yl)-(toluene-4-sulfonyl)-amino]-N-methoxy-N-methyl-acetamide

Guidance literature:: Multi-step reaction with 6 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

With pyridine; 2,6-dimethylpyridine; methanol; sodium tetrahydroborate; 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