(2R,5S,6S,9R)-2-tert-Butyl-6-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-2-methyl-hex-1-enyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-one

Base Information

Chemical Name:(2R,5S,6S,9R)-2-tert-Butyl-6-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-2-methyl-hex-1-enyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-one
CAS No.:496918-23-1
Molecular Formula:C₄₃H₆₆O₇Si₂
Molecular Weight:751.164
Hs Code.:

(2R,5S,6S,9R)-2-tert-Butyl-6-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-2-methyl-hex-1-enyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-one

Synonyms:(2R,5S,6S,9R)-2-tert-Butyl-6-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-2-methyl-hex-1-enyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-one

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Chemical Property of (2R,5S,6S,9R)-2-tert-Butyl-6-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-2-methyl-hex-1-enyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-one

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Technology Process of (2R,5S,6S,9R)-2-tert-Butyl-6-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-2-methyl-hex-1-enyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-one

There total 6 articles about (2R,5S,6S,9R)-2-tert-Butyl-6-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-2-methyl-hex-1-enyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-one 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: 71.0%

: 214198-28-4
(2R,5S,6S,9R)-2-tert-Butyl-6-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-hexa-1,5-dienyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-one

: 496918-23-1
(2R,5S,6S,9R)-2-tert-Butyl-6-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-2-methyl-hex-1-enyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-one

Guidance literature:: With osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; toluene; tert-butyl alcohol; for 24h;
DOI:10.3987/com-02-s(m)17

Reference yield:

: 146983-25-7
(E)-3-[(2R,5S,6S,9R)-2-tert-Butyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-4-oxo-1,3-dioxa-spiro[4.5]dec-7-en-6-yl]-2-methyl-acrylic acid ethyl ester

: 496918-23-1
(2R,5S,6S,9R)-2-tert-Butyl-6-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-2-methyl-hex-1-enyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-one

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / DIBAL-H / CH₂Cl₂ / -78 °C

2: 92 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1 h / -78 °C

3: toluene / 5 h / -78 °C

4: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

5: 71 percent / (DHQD)2-PHAL; Ad-mix β; OsO4 / 2-methyl-propan-2-ol; H2O; toluene / 24 h

With 2,6-dimethylpyridine; osmium(VIII) oxide; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; In dichloromethane; water; toluene; tert-butyl alcohol; 2: Swern oxidation / 5: Sharpless dihydroxylation;
DOI:10.3987/com-02-s(m)17

Reference yield:

: 497065-29-9
(2R,2R,4S,5R)-spiro-1-[(tert-butyldiphenylsilyloxy)methyl]-2-methyl-5-(2-methylpropen-1-ol)cyclohex-1-ene-(4,5')-2'-tert-butyl-1',3'-dioxolan-4'-ol

: 496918-23-1
(2R,5S,6S,9R)-2-tert-Butyl-6-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-2-methyl-hex-1-enyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-one

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1 h / -78 °C

2: toluene / 5 h / -78 °C

3: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

4: 71 percent / (DHQD)2-PHAL; Ad-mix β; OsO4 / 2-methyl-propan-2-ol; H2O; toluene / 24 h

With 2,6-dimethylpyridine; osmium(VIII) oxide; oxalyl dichloride; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; In dichloromethane; water; toluene; tert-butyl alcohol; 1: Swern oxidation / 4: Sharpless dihydroxylation;
DOI:10.3987/com-02-s(m)17