(1S,2S,2'S,4a'R,5S,7a'R)-2-allyl-4-((tert-butyldiphenylsilyloxy)methyl)-4a',5-dimethyl-2'-((2R,4S)-4-methylhex-5-en-2-yl)-2',3'-dihydrospiro[cyclohex[3]ene-1,7'-furo[3,4-b]pyran]-4',5'(4a'H,7a'H)-dione

Base Information

Chemical Name:(1S,2S,2'S,4a'R,5S,7a'R)-2-allyl-4-((tert-butyldiphenylsilyloxy)methyl)-4a',5-dimethyl-2'-((2R,4S)-4-methylhex-5-en-2-yl)-2',3'-dihydrospiro[cyclohex[3]ene-1,7'-furo[3,4-b]pyran]-4',5'(4a'H,7a'H)-dione
CAS No.:1314123-82-4
Molecular Formula:C₄₁H₅₄O₅Si
Molecular Weight:654.962
Hs Code.:

(1S,2S,2'S,4a'R,5S,7a'R)-2-allyl-4-((tert-butyldiphenylsilyloxy)methyl)-4a',5-dimethyl-2'-((2R,4S)-4-methylhex-5-en-2-yl)-2',3'-dihydrospiro[cyclohex[3]ene-1,7'-furo[3,4-b]pyran]-4',5'(4a'H,7a'H)-dione

Synonyms:(1S,2S,2'S,4a'R,5S,7a'R)-2-allyl-4-((tert-butyldiphenylsilyloxy)methyl)-4a',5-dimethyl-2'-((2R,4S)-4-methylhex-5-en-2-yl)-2',3'-dihydrospiro[cyclohex[3]ene-1,7'-furo[3,4-b]pyran]-4',5'(4a'H,7a'H)-dione

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Chemical Property of (1S,2S,2'S,4a'R,5S,7a'R)-2-allyl-4-((tert-butyldiphenylsilyloxy)methyl)-4a',5-dimethyl-2'-((2R,4S)-4-methylhex-5-en-2-yl)-2',3'-dihydrospiro[cyclohex[3]ene-1,7'-furo[3,4-b]pyran]-4',5'(4a'H,7a'H)-dione

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Technology Process of (1S,2S,2'S,4a'R,5S,7a'R)-2-allyl-4-((tert-butyldiphenylsilyloxy)methyl)-4a',5-dimethyl-2'-((2R,4S)-4-methylhex-5-en-2-yl)-2',3'-dihydrospiro[cyclohex[3]ene-1,7'-furo[3,4-b]pyran]-4',5'(4a'H,7a'H)-dione

There total 14 articles about (1S,2S,2'S,4a'R,5S,7a'R)-2-allyl-4-((tert-butyldiphenylsilyloxy)methyl)-4a',5-dimethyl-2'-((2R,4S)-4-methylhex-5-en-2-yl)-2',3'-dihydrospiro[cyclohex[3]ene-1,7'-furo[3,4-b]pyran]-4',5'(4a'H,7a'H)-dione 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: 60.0%

: 1314123-90-4
(1S,2S,2'S,4a'R,5S,7a'R)-4-((tert-butyldiphenylsilyloxy)methyl)-2-(3-hydroxypropyl)-4a',5-dimethyl-2'-((2R,4S)-4-methylhex-5-en-2-yl)-2',3'-dihydrospiro[cyclohex[3]ene-1,7'-furo[3,4-b]pyran]-4',5'(4a'H,7a'H)-dione

: 1314123-82-4
(1S,2S,2'S,4a'R,5S,7a'R)-2-allyl-4-((tert-butyldiphenylsilyloxy)methyl)-4a',5-dimethyl-2'-((2R,4S)-4-methylhex-5-en-2-yl)-2',3'-dihydrospiro[cyclohex[3]ene-1,7'-furo[3,4-b]pyran]-4',5'(4a'H,7a'H)-dione

Guidance literature:: (1S,2S,2'S,4a'R,5S,7a'R)-4-((tert-butyldiphenylsilyloxy)methyl)-2-(3-hydroxypropyl)-4a',5-dimethyl-2'-((2R,4S)-4-methylhex-5-en-2-yl)-2',3'-dihydrospiro[cyclohex[3]ene-1,7'-furo[3,4-b]pyran]-4',5'(4a'H,7a'H)-dione; With ortho-nitrophenyl selenocyanate; tributylphosphine; In tetrahydrofuran; for 1h; Inert atmosphere;

With dihydrogen peroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 18h; Inert atmosphere;
DOI:10.1002/anie.201102037

Reference yield:

: C₄₇H₅₉NO₇SeSi

: 1314123-82-4
(1S,2S,2'S,4a'R,5S,7a'R)-2-allyl-4-((tert-butyldiphenylsilyloxy)methyl)-4a',5-dimethyl-2'-((2R,4S)-4-methylhex-5-en-2-yl)-2',3'-dihydrospiro[cyclohex[3]ene-1,7'-furo[3,4-b]pyran]-4',5'(4a'H,7a'H)-dione

Guidance literature:: With dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 18h; Inert atmosphere;
DOI:10.1002/anie.201102037

Reference yield:

: 1314123-86-8
6-((2S,3R,5S)-2-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-3,5-dimethylheptyl)-2,2-dimethyl-4H-1,3-dioxin-4-one

: 1314123-82-4
(1S,2S,2'S,4a'R,5S,7a'R)-2-allyl-4-((tert-butyldiphenylsilyloxy)methyl)-4a',5-dimethyl-2'-((2R,4S)-4-methylhex-5-en-2-yl)-2',3'-dihydrospiro[cyclohex[3]ene-1,7'-furo[3,4-b]pyran]-4',5'(4a'H,7a'H)-dione

Guidance literature:: Multi-step reaction with 12 steps

1.1: methanol; ammonium fluoride / 24 h / 40 °C / Inert atmosphere

2.1: ortho-nitrophenyl selenocyanate; tributylphosphine / tetrahydrofuran / 0.5 h / 23 °C / Inert atmosphere

2.2: 12 h / 0 °C / Inert atmosphere

3.1: dichloromethane / 4.5 h / 0 - 20 °C / Inert atmosphere

4.1: pyridine hydrofluoride / tetrahydrofuran / 48 h / 0 - 20 °C / Inert atmosphere

5.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.75 h / -78 - -40 °C / Inert atmosphere

6.1: hydrogen fluoride; water / acetonitrile / 18 h / 20 °C / Inert atmosphere

7.1: potassium tert-butylate / tetrahydrofuran / 0.25 h / Inert atmosphere

7.2: Inert atmosphere

8.1: potassium carbonate / acetonitrile / 2 h / 70 °C / Inert atmosphere

9.1: 1H-imidazole / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

10.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 22 h / Inert atmosphere

11.1: tributylphosphine / tetrahydrofuran / 1 h / Inert atmosphere

12.1: dihydrogen peroxide / tetrahydrofuran; water / 18 h / 0 °C / Inert atmosphere

With 1H-imidazole; methanol; ammonium fluoride; ortho-nitrophenyl selenocyanate; tributylphosphine; pyridine hydrofluoride; trimethylsilyl trifluoromethanesulfonate; hydrogen fluoride; potassium tert-butylate; water; dihydrogen peroxide; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; acetonitrile; 2.1: Grieco elimination / 2.2: Grieco elimination;
DOI:10.1002/anie.201102037