(2R,5S,6S,9R)-2-tert-Butyl-6-[(1E,5E,7E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-8-iodo-2,6-dimethyl-octa-1,5,7-trienyl]-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-[(1E,5E,7E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-8-iodo-2,6-dimethyl-octa-1,5,7-trienyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-one
CAS No.:299179-94-5
Molecular Formula:C₄₆H₆₇IO₅Si₂
Molecular Weight:883.11
Hs Code.:

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

There total 8 articles about (2R,5S,6S,9R)-2-tert-Butyl-6-[(1E,5E,7E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-8-iodo-2,6-dimethyl-octa-1,5,7-trienyl]-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: 82.0%

: 75-47-8
iodoform

: 496918-01-5
(2E,6E)-(S)-7-[(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]-5-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-hepta-2,6-dienal

: 299179-94-5
(2R,5S,6S,9R)-2-tert-Butyl-6-[(1E,5E,7E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-8-iodo-2,6-dimethyl-octa-1,5,7-trienyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-one

Guidance literature:: With chromium dichloride; In tetrahydrofuran; at 20 ℃; for 1.5h;
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

: 299179-94-5
(2R,5S,6S,9R)-2-tert-Butyl-6-[(1E,5E,7E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-8-iodo-2,6-dimethyl-octa-1,5,7-trienyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-one

Guidance literature:: Multi-step reaction with 8 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

6: 94 percent / periodic acid / tetrahydrofuran / 2 h / 20 °C

7: 83 percent / toluene / 20 h / 85 °C

8: 82 percent / CrCl₂ / tetrahydrofuran / 1.5 h / 20 °C

With 2,6-dimethylpyridine; chromium dichloride; osmium(VIII) oxide; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; periodic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; 2: Swern oxidation / 5: Sharpless dihydroxylation / 8: Takai reaction;
DOI:10.3987/com-02-s(m)17

Reference yield:

: 496917-91-0
(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-propenal

: 299179-94-5
(2R,5S,6S,9R)-2-tert-Butyl-6-[(1E,5E,7E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-8-iodo-2,6-dimethyl-octa-1,5,7-trienyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-one

Guidance literature:: Multi-step reaction with 6 steps

1: toluene / 5 h / -78 °C

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

3: 71 percent / (DHQD)2-PHAL; Ad-mix β; OsO4 / 2-methyl-propan-2-ol; H2O; toluene / 24 h

4: 94 percent / periodic acid / tetrahydrofuran / 2 h / 20 °C

5: 83 percent / toluene / 20 h / 85 °C

6: 82 percent / CrCl₂ / tetrahydrofuran / 1.5 h / 20 °C

With 2,6-dimethylpyridine; chromium dichloride; osmium(VIII) oxide; periodic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; 3: Sharpless dihydroxylation / 6: Takai reaction;
DOI:10.3987/com-02-s(m)17