(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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Chemical Name:(3S,3aR,5S,7S,7aS)-3-Benzyloxy-5-isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-octahydro-pyrano[3,4-b]pyrrole
CAS No.:871483-77-1
Molecular Formula:C₃₅H₅₅NO₆SSi
Molecular Weight:645.976
Hs Code.:

Synonyms:(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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Chemical Property of (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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Technology Process of (3S,3aR,5S,7S,7aS)-3-Benzyloxy-5-isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-octahydro-pyrano[3,4-b]pyrrole

There total 11 articles about (3S,3aR,5S,7S,7aS)-3-Benzyloxy-5-isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-octahydro-pyrano[3,4-b]pyrrole 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: 92.0%

: 871483-76-0
(3S,3aR,5S,7S,7aS)-5-Isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-octahydro-pyrano[3,4-b]pyrrol-3-ol

: 100-39-0
benzyl bromide

: 871483-77-1
(3S,3aR,5S,7S,7aS)-3-Benzyloxy-5-isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-octahydro-pyrano[3,4-b]pyrrole

Guidance literature:: With sodium hydride; In tetrahydrofuran;
DOI:10.1016/j.bmcl.2005.08.062

Reference yield:

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

: 871483-77-1
(3S,3aR,5S,7S,7aS)-3-Benzyloxy-5-isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-octahydro-pyrano[3,4-b]pyrrole

Guidance literature:: Multi-step reaction with 9 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

7: 96 percent / NaBH₄; CeCl₃*7H₂O / methanol

8: 78 percent / (PPh₃)3RhCl; H₂

9: 92 percent / NaH / tetrahydrofuran

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; Wilkinson's catalyst; n-butyllithium; cerium(III) chloride; oxalyl dichloride; di-isopropyl azodicarboxylate; hydrogen; iodine; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 2: Swern oxidation / 4: Luche reduction / 5: Mitsunobu reaction / 7: Luche reduction;
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

: 871483-77-1
(3S,3aR,5S,7S,7aS)-3-Benzyloxy-5-isobutoxy-1-(toluene-4-sulfonyl)-7-triisopropylsilanyloxymethyl-octahydro-pyrano[3,4-b]pyrrole

Guidance literature:: Multi-step reaction with 10 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

8: 96 percent / NaBH₄; CeCl₃*7H₂O / methanol

9: 78 percent / (PPh₃)3RhCl; H₂

10: 92 percent / NaH / tetrahydrofuran

With pyridine; 2,6-dimethylpyridine; methanol; sodium tetrahydroborate; Wilkinson's catalyst; n-butyllithium; cerium(III) chloride; oxalyl dichloride; di-isopropyl azodicarboxylate; hydrogen; iodine; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 3: Swern oxidation / 5: Luche reduction / 6: Mitsunobu reaction / 8: Luche reduction;
DOI:10.1016/j.bmcl.2005.08.062