(3R,4S,5R,6S,8R,9S,10R,11R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-1,12-diene-3,11-diol

Base Information

Chemical Name:(3R,4S,5R,6S,8R,9S,10R,11R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-1,12-diene-3,11-diol
CAS No.:846577-26-2
Molecular Formula:C₄₃H₇₂O₈Si₂
Molecular Weight:773.211
Hs Code.:

Synonyms:(3R,4S,5R,6S,8R,9S,10R,11R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-1,12-diene-3,11-diol

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Chemical Property of (3R,4S,5R,6S,8R,9S,10R,11R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-1,12-diene-3,11-diol

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Technology Process of (3R,4S,5R,6S,8R,9S,10R,11R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-1,12-diene-3,11-diol

There total 13 articles about (3R,4S,5R,6S,8R,9S,10R,11R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-1,12-diene-3,11-diol 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:

: C₄₃H₇₀I₂O₈Si₂

: 846577-26-2
(3R,4S,5R,6S,8R,9S,10R,11R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-1,12-diene-3,11-diol

Guidance literature:: With zinc; iodine; In methanol; for 0.5h; Heating;
DOI:10.1021/ol0473400

Reference yield:

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

: 846577-26-2
(3R,4S,5R,6S,8R,9S,10R,11R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-1,12-diene-3,11-diol

Guidance literature:: Multi-step reaction with 12 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

10.1: 94 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

11.1: NaI / butan-2-one / 2 h / Heating

12.1: 1.12 g / Zn / I₂ / methanol / 0.5 h / Heating

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; sodium iodide; zinc; iodine; In tetrahydrofuran; methanol; decane; hexane; dichloromethane; toluene; butanone; 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

: 846577-26-2
(3R,4S,5R,6S,8R,9S,10R,11R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-1,12-diene-3,11-diol

Guidance literature:: Multi-step reaction with 10 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

8.1: 94 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

9.1: NaI / butan-2-one / 2 h / Heating

10.1: 1.12 g / Zn / I₂ / methanol / 0.5 h / Heating

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