(2S,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxirane-2-carbaldehyde

Base Information

Chemical Name:(2S,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxirane-2-carbaldehyde
CAS No.:170706-59-9
Molecular Formula:C₃₁H₄₄O₆Si
Molecular Weight:540.772
Hs Code.:

(2S,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxirane-2-carbaldehyde

Synonyms:(2S,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxirane-2-carbaldehyde

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Chemical Property of (2S,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxirane-2-carbaldehyde

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Technology Process of (2S,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxirane-2-carbaldehyde

There total 8 articles about (2S,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxirane-2-carbaldehyde 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: 94.0%

: 170706-58-8
{(2R,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-methanol

: 170706-59-9
(2S,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxirane-2-carbaldehyde

Guidance literature:: With pyridine-SO₃ complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 0 ℃; for 4h;
DOI:10.1021/ja00146a008

Reference yield:

: 131310-62-8
tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-6-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane

: 170706-59-9
(2S,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxirane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / CSA / methanol / 1 h / 0 °C

2: 90 percent / KH / tetrahydrofuran / 1 h / 45 °C

3: 1.) 9-BBN, 2.) 3 N NaOH, 30percent aq. H₂O₂ / 1.) THF, 25 deg C, 1.5 h, 2.) THF, 0 deg C, 1 h

4: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

5: 90 percent / benzene / 1 h / 50 °C

6: 96 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

7: 92 percent / (-)-diethyl tartrate, Ti(O-i-Pr)4, tert-BuOOH / CH₂Cl₂ / 14 h / -25 °C

8: 94 percent / SO₃*pyridine, Et₃N / CH₂Cl₂; dimethylsulfoxide / 4 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO₃ complex; camphor-10-sulfonic acid; dihydrogen peroxide; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; benzene;
DOI:10.1021/ja00146a008

Reference yield:

: 170706-52-2
(2R,3S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-6-methyl-6-vinyl-tetrahydro-pyran-3-ol

: 170706-59-9
(2S,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxirane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / KH / tetrahydrofuran / 1 h / 45 °C

2: 1.) 9-BBN, 2.) 3 N NaOH, 30percent aq. H₂O₂ / 1.) THF, 25 deg C, 1.5 h, 2.) THF, 0 deg C, 1 h

3: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

4: 90 percent / benzene / 1 h / 50 °C

5: 96 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

6: 92 percent / (-)-diethyl tartrate, Ti(O-i-Pr)4, tert-BuOOH / CH₂Cl₂ / 14 h / -25 °C

7: 94 percent / SO₃*pyridine, Et₃N / CH₂Cl₂; dimethylsulfoxide / 4 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO₃ complex; dihydrogen peroxide; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; benzene;
DOI:10.1021/ja00146a008