[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-methanol

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Chemical Name:[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-methanol
CAS No.:284035-53-6
Molecular Formula:C₂₅H₄₄O₅Si
Molecular Weight:452.707
Hs Code.:

Synonyms:[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-methanol

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Chemical Property of [(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-methanol

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Technology Process of [(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-methanol

There total 7 articles about [(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-methanol 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%

: 284035-52-5
Benzoic acid (2R,4S,5S,6R)-6-(4-benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

: 284035-53-6
[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: With potassium hydroxide; In methanol; at 20 ℃; for 1h;
DOI:10.1016/S0040-4039(00)00383-X

Reference yield:

: 78999-24-3
5-benzyloxy-1-pentanal

: 284035-53-6
[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 78 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / 3 h / -78 - 0 °C

2.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

3.1: 74 percent / NaBH₄ / tetrahydrofuran; H₂O / 48 h / 20 °C

4.1: 97 percent / SO₃*Py; Et₃N / dimethylsulfoxide / 1 h / 20 °C

5.1: Bu₂BOTf / CH₂Cl₂ / 3 h / -78 - 0 °C

5.2: TBAF / tetrahydrofuran / 3 h / 20 °C

5.3: 58 percent / CSA / 1 h / 20 °C

6.1: 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

7.1: 92 percent / KOH / methanol / 1 h / 20 °C

With 2,6-dimethylpyridine; potassium hydroxide; sodium tetrahydroborate; pyridine-SO₃ complex; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; 1.1: aldol coupling / 2.1: Etherification / 3.1: Reduction / 4.1: Oxidation / 5.1: aldol reaction / 5.2: deprotection / 5.3: ketalization / 6.1: Etherification / 7.1: Hydrolysis;
DOI:10.1016/S0040-4039(00)00383-X

Reference yield:

: 171189-79-0
(S)-4-Benzyl-3-((2S,3R)-7-benzyloxy-3-hydroxy-2-methyl-heptanoyl)-oxazolidin-2-one

: 284035-53-6
[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

2.1: 74 percent / NaBH₄ / tetrahydrofuran; H₂O / 48 h / 20 °C

3.1: 97 percent / SO₃*Py; Et₃N / dimethylsulfoxide / 1 h / 20 °C

4.1: Bu₂BOTf / CH₂Cl₂ / 3 h / -78 - 0 °C

4.2: TBAF / tetrahydrofuran / 3 h / 20 °C

4.3: 58 percent / CSA / 1 h / 20 °C

5.1: 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

6.1: 92 percent / KOH / methanol / 1 h / 20 °C

With 2,6-dimethylpyridine; potassium hydroxide; sodium tetrahydroborate; pyridine-SO₃ complex; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; 1.1: Etherification / 2.1: Reduction / 3.1: Oxidation / 4.1: aldol reaction / 4.2: deprotection / 4.3: ketalization / 5.1: Etherification / 6.1: Hydrolysis;
DOI:10.1016/S0040-4039(00)00383-X