(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

Base Information

• Chemical Name: (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
• CAS No.: 1314123-90-4
• Molecular Formula: C₄₁H₅₆O₆Si
• Molecular Weight: 672.978

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (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

There total 14 articles about (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 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: 62.0%

(1S,2S,2'S,4a'R,5S,7a'R)-2-(3-(benzyloxy)propyl)-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 (1314123-89-1) → (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 (1314123-90-4)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 22h; Inert atmosphere;

DOI:10.1002/anie.201102037

Reference yield:

6-((2S,3R,5S)-2-(tert-butyldimethylsilyloxy)-7-hydroxy-3,5-dimethylheptyl)-2,2-dimethyl-4H-1,3-dioxin-4-one (1314123-87-9) → (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 (1314123-90-4)

Guidance literature:

Multi-step reaction with 9 steps

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

1.2: 12 h / 0 °C / Inert atmosphere

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

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

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

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

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

6.2: Inert atmosphere

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

8.1: 1H-imidazole / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

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

With 1H-imidazole; ortho-nitrophenyl selenocyanate; tributylphosphine; pyridine hydrofluoride; trimethylsilyl trifluoromethanesulfonate; hydrogen fluoride; potassium tert-butylate; water; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; acetonitrile; 1.1: Grieco elimination / 1.2: Grieco elimination;

DOI:10.1002/anie.201102037

Reference yield:

6-((3R,5S)-7-(tert-butyldiphenylsilyloxy)-2-hydroxy-3,5-dimethylheptyl)-2,2-dimethyl-4H-1,3-dioxin-4-one → (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 (1314123-90-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

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

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

3.2: 12 h / 0 °C / Inert atmosphere

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

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

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

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

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

8.2: Inert atmosphere

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

10.1: 1H-imidazole / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

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

With 1H-imidazole; 2,6-dimethylpyridine; methanol; ammonium fluoride; ortho-nitrophenyl selenocyanate; tributylphosphine; pyridine hydrofluoride; trimethylsilyl trifluoromethanesulfonate; hydrogen fluoride; potassium tert-butylate; water; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; acetonitrile; 3.1: Grieco elimination / 3.2: Grieco elimination;

DOI:10.1002/anie.201102037

upstream raw materials:

(1S,2S,5S)-2-(3-(benzyloxy)propyl)-1-(tert-butyldimethylsilyloxy)-4-((tertbutyldiphenylsilyloxy)methyl)-5-methylcyclohex-3-enecarbaldehyde

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

6-((2S,3R,5S)-2-(tert-butyldimethylsilyloxy)-7-hydroxy-3,5-dimethylheptyl)-2,2-dimethyl-4H-1,3-dioxin-4-one

6-((2S,3R,5S)-2-(tert-butyldimethylsilyloxy)-3,5-dimethylhept-6-enyl)-2,2-dimethyl-4H-1,3-dioxin-4-one

Downstream raw materials:

(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

C₃₉H₅₂O₅Si

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