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

Base Information

Chemical Name:{(2R,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-methanol
CAS No.:170706-58-8
Molecular Formula:C₃₁H₄₆O₆Si
Molecular Weight:542.788
Hs Code.:

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

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

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

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

There total 7 articles about {(2R,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-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%

: 170706-57-7
(E)-4-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-but-2-en-1-ol

: 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

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; (-)-diethyl tartrate; In dichloromethane; at -25 ℃; for 14h;
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

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

Guidance literature:: Multi-step reaction with 7 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

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

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

Guidance literature:: Multi-step reaction with 6 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

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