(5S,6R,9R)-8-Benzyloxymethyl-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

Base Information

Chemical Name:(5S,6R,9R)-8-Benzyloxymethyl-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one
CAS No.:141293-00-7
Molecular Formula:C₃₀H₄₄O₆Si
Molecular Weight:528.761
Hs Code.:

(5S,6R,9R)-8-Benzyloxymethyl-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

Synonyms:(5S,6R,9R)-8-Benzyloxymethyl-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

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Chemical Property of (5S,6R,9R)-8-Benzyloxymethyl-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

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Technology Process of (5S,6R,9R)-8-Benzyloxymethyl-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

There total 34 articles about (5S,6R,9R)-8-Benzyloxymethyl-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-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:

: 40665-79-0
(3-benzyloxy-2-oxopropyl)phosphonic acid dimethyl ester

: 141293-00-7
(5R,6S,9S)-8-Benzyloxymethyl-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

Guidance literature:: Multi-step reaction with 16 steps

1: 75 percent / K₂CO₃, 18-crown-6 / acetonitrile

2: 86 percent / DMPU / tetrahydrofuran

3: 91 percent / TBAF

4: 100 percent / DMSO

5: 83 percent / CH₂Cl₂

6: 95 percent / DIBAH

7: 93 percent / imidazole

8: 88 percent / chiral N-tosyl-4-methylindol-3-yl-oxazaborolidin-3-one / CH₂Cl₂ / 8 h / -78 - -40 °C

9: 99 percent / NaBH₄ / methanol

10: 98 percent / NaOMe / methanol / 5 h / Ambient temperature

11: 96 percent / NaOH / 2-methyl-propan-2-ol

12: MCPBA / CH₂Cl₂

13: 90 percent / NaOAC / 125 °C

14: 90 percent / NaClO₂ / 2-methyl-propan-2-ol; H₂O

15: 100 percent

16: 1) LiN(TMS)2, DMPU / 1) THF

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydroxide; sodium chlorite; sodium tetrahydroborate; 18-crown-6 ether; tetrabutyl ammonium fluoride; sodium methylate; sodium acetate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; chiral N-tosyl-4-methylindol-3-yl-oxazaborolidin-3-one; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo00037a005

Reference yield:

: 40665-79-0
(3-benzyloxy-2-oxopropyl)phosphonic acid dimethyl ester

: 141293-00-7
(5S,6R,9R)-8-Benzyloxymethyl-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

Guidance literature:: Multi-step reaction with 16 steps

1: 75 percent / K₂CO₃, 18-crown-6 / acetonitrile

2: 86 percent / DMPU / tetrahydrofuran

3: 91 percent / TBAF

4: 100 percent / DMSO

5: 83 percent / CH₂Cl₂

6: 95 percent / DIBAH

7: 93 percent / imidazole

8: 88 percent / chiral N-tosyl-4-methylindol-3-yl-oxazaborolidin-3-one / CH₂Cl₂ / 8 h / -78 - -40 °C

9: 99 percent / NaBH₄ / methanol

10: 98 percent / NaOMe / methanol / 5 h / Ambient temperature

11: 96 percent / NaOH / 2-methyl-propan-2-ol

12: MCPBA / CH₂Cl₂

13: 90 percent / NaOAC / 125 °C

14: 90 percent / NaClO₂ / 2-methyl-propan-2-ol; H₂O

15: 100 percent

16: 1) LiN(TMS)2, DMPU / 1) THF

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydroxide; sodium chlorite; sodium tetrahydroborate; 18-crown-6 ether; tetrabutyl ammonium fluoride; sodium methylate; sodium acetate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; chiral N-tosyl-4-methylindol-3-yl-oxazaborolidin-3-one; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo00037a005

Reference yield:

: 141292-86-6
(2E,4Z)-4-Benzyloxymethyl-hexa-2,4-dien-1-ol

: 141293-00-7
(5R,6S,9S)-8-Benzyloxymethyl-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

Guidance literature:: Multi-step reaction with 13 steps

1: 100 percent / DMSO

2: 83 percent / CH₂Cl₂

3: 95 percent / DIBAH

4: 93 percent / imidazole

5: 88 percent / chiral N-tosyl-4-methylindol-3-yl-oxazaborolidin-3-one / CH₂Cl₂ / 8 h / -78 - -40 °C

6: 99 percent / NaBH₄ / methanol

7: 98 percent / NaOMe / methanol / 5 h / Ambient temperature

8: 96 percent / NaOH / 2-methyl-propan-2-ol

9: MCPBA / CH₂Cl₂

10: 90 percent / NaOAC / 125 °C

11: 90 percent / NaClO₂ / 2-methyl-propan-2-ol; H₂O

12: 100 percent

13: 1) LiN(TMS)2, DMPU / 1) THF

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium methylate; sodium acetate; diisobutylaluminium hydride; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; chiral N-tosyl-4-methylindol-3-yl-oxazaborolidin-3-one; In methanol; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo00037a005