{(2S,3S)-3-[(1R,2R,3S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((2S,3S)-3-hydroxymethyl-oxiranyl)-2,6-bis-(4-methoxy-benzyloxy)-1-methyl-octyl]-oxiranyl}-methanol

Base Information

Chemical Name:{(2S,3S)-3-[(1R,2R,3S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((2S,3S)-3-hydroxymethyl-oxiranyl)-2,6-bis-(4-methoxy-benzyloxy)-1-methyl-octyl]-oxiranyl}-methanol
CAS No.:846577-25-1
Molecular Formula:C₄₃H₇₂O₁₀Si₂
Molecular Weight:805.21
Hs Code.:

{(2S,3S)-3-[(1R,2R,3S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((2S,3S)-3-hydroxymethyl-oxiranyl)-2,6-bis-(4-methoxy-benzyloxy)-1-methyl-octyl]-oxiranyl}-methanol

Synonyms:{(2S,3S)-3-[(1R,2R,3S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((2S,3S)-3-hydroxymethyl-oxiranyl)-2,6-bis-(4-methoxy-benzyloxy)-1-methyl-octyl]-oxiranyl}-methanol

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Chemical Property of {(2S,3S)-3-[(1R,2R,3S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((2S,3S)-3-hydroxymethyl-oxiranyl)-2,6-bis-(4-methoxy-benzyloxy)-1-methyl-octyl]-oxiranyl}-methanol

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Technology Process of {(2S,3S)-3-[(1R,2R,3S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((2S,3S)-3-hydroxymethyl-oxiranyl)-2,6-bis-(4-methoxy-benzyloxy)-1-methyl-octyl]-oxiranyl}-methanol

There total 10 articles about {(2S,3S)-3-[(1R,2R,3S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((2S,3S)-3-hydroxymethyl-oxiranyl)-2,6-bis-(4-methoxy-benzyloxy)-1-methyl-octyl]-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: 68.0%

: 846577-24-0
(2E,11E)-(4S,5R,6S,8R,9S,10R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-2,11-diene-1,13-diol

: 846577-25-1
{(2S,3S)-3-[(1R,2R,3S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((2S,3S)-3-hydroxymethyl-oxiranyl)-2,6-bis-(4-methoxy-benzyloxy)-1-methyl-octyl]-oxiranyl}-methanol

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; In decane; dichloromethane; at -20 ℃;
DOI:10.1021/ol0473400

Reference yield:

: (2S,4R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-pentanedial

: 846577-25-1
{(2S,3S)-3-[(1R,2R,3S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((2S,3S)-3-hydroxymethyl-oxiranyl)-2,6-bis-(4-methoxy-benzyloxy)-1-methyl-octyl]-oxiranyl}-methanol

Guidance literature:: Multi-step reaction with 9 steps

1.1: KHMDS; 18-C-6 / tetrahydrofuran / 0.25 h / -78 °C

1.2: 6.3 g / tetrahydrofuran / -78 - 20 °C

2.1: 100 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

3.1: BH₃*THF / tetrahydrofuran / 0.75 h

3.2: 70 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 1 h / 20 °C

4.1: PPTS / CH₂Cl₂ / 20 °C

5.1: 2.03 g / DIBAL / toluene / -78 - 0 °C

6.1: 97 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

7.1: NaH / tetrahydrofuran / -78 °C

7.2: 96 percent / tetrahydrofuran / -78 - 20 °C

8.1: 97 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

9.1: 68 percent / Ti(OiPr)4; L-(+)-DET; tert-butyl hydroperoxide / CH₂Cl₂; decane / -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; borane-THF; oxalyl dichloride; 18-crown-6 ether; diethyl (2R,3R)-tartrate; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; decane; hexane; dichloromethane; toluene; 6.1: Swern oxidation / 7.2: Horner-Wadsworth-Emmons reaction / 9.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol0473400

Reference yield:

: 846577-21-7
(2Z,7Z)-(4S,6R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2,8-dimethyl-nona-2,7-diene-1,9-diol

: 846577-25-1
{(2S,3S)-3-[(1R,2R,3S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((2S,3S)-3-hydroxymethyl-oxiranyl)-2,6-bis-(4-methoxy-benzyloxy)-1-methyl-octyl]-oxiranyl}-methanol

Guidance literature:: Multi-step reaction with 7 steps

1.1: BH₃*THF / tetrahydrofuran / 0.75 h

1.2: 70 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 1 h / 20 °C

2.1: PPTS / CH₂Cl₂ / 20 °C

3.1: 2.03 g / DIBAL / toluene / -78 - 0 °C

4.1: 97 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

5.1: NaH / tetrahydrofuran / -78 °C

5.2: 96 percent / tetrahydrofuran / -78 - 20 °C

6.1: 97 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

7.1: 68 percent / Ti(OiPr)4; L-(+)-DET; tert-butyl hydroperoxide / CH₂Cl₂; decane / -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; borane-THF; oxalyl dichloride; diethyl (2R,3R)-tartrate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; decane; hexane; dichloromethane; toluene; 4.1: Swern oxidation / 5.2: Horner-Wadsworth-Emmons reaction / 7.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol0473400