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

Base Information

• Chemical Name: 6-((2S,3R,5S)-2-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-3,5-dimethylheptyl)-2,2-dimethyl-4H-1,3-dioxin-4-one
• CAS No.: 1314123-86-8
• Molecular Formula: C₃₇H₅₈O₅Si₂
• Molecular Weight: 639.036

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 6-((2S,3R,5S)-2-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-3,5-dimethylheptyl)-2,2-dimethyl-4H-1,3-dioxin-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: 92.0%

6-((3R,5S)-7-(tert-butyldiphenylsilyloxy)-2-hydroxy-3,5-dimethylheptyl)-2,2-dimethyl-4H-1,3-dioxin-4-one + t-butyldimethylsiyl triflate (69739-34-0) → 6-((2S,3R,5S)-2-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-3,5-dimethylheptyl)-2,2-dimethyl-4H-1,3-dioxin-4-one (1314123-86-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/anie.201102037

Reference yield:

6-((2S,3R,5S)-2-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-3,5-dimethylheptyl)-2,2-dimethyl-4H-1,3-dioxin-4-one (1314123-86-8) → (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 (1314123-82-4)

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

Reference yield:

6-((2S,3R,5S)-2-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-3,5-dimethylheptyl)-2,2-dimethyl-4H-1,3-dioxin-4-one (1314123-86-8) → C39H50O5Si

Guidance literature:

Multi-step reaction with 13 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

13.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / Reflux

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 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

upstream raw materials:

t-butyldimethylsiyl triflate

Downstream raw materials:

(2R,6S)-ethyl 2-((1S,2S,5S)-2-(3-(benzyloxy)propyl)-1-(tert-butyldimethylsilyloxy)-4-((tert-butyldiphenylsilyloxy)methyl)-5-methylcyclohex-3-enyl)-6-((2R,4S)-4-methylhex-5-en-2-yl)-4-oxotetrahydro-2H-pyran-3-carboxylate

(1S,2S,2'S,4a'R,5S,7a'R)-2-(3-(benzyloxy)propyl)-4-(hydroxymethyl)-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

(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

(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

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