(2RS,5RS,8SR,9SR,10RS)-8,9-bis(methoxymethoxy)-6,10-dimethyl-2-pivaloyloxyspiro<4.5>dec-6-ene

Base Information

• Chemical Name: (2RS,5RS,8SR,9SR,10RS)-8,9-bis(methoxymethoxy)-6,10-dimethyl-2-pivaloyloxyspiro<4.5>dec-6-ene
• CAS No.: 101467-36-1
• Molecular Formula: C₂₁H₃₆O₆
• Molecular Weight: 384.513
• Mol file: 101467-36-1.mol

Synonyms:(2RS,5RS,8SR,9SR,10RS)-8,9-bis(methoxymethoxy)-6,10-dimethyl-2-pivaloyloxyspiro<4.5>dec-6-ene

Chemical Property of (2RS,5RS,8SR,9SR,10RS)-8,9-bis(methoxymethoxy)-6,10-dimethyl-2-pivaloyloxyspiro<4.5>dec-6-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2RS,5RS,8SR,9SR,10RS)-8,9-bis(methoxymethoxy)-6,10-dimethyl-2-pivaloyloxyspiro<4.5>dec-6-ene

There total 1 articles about (2RS,5RS,8SR,9SR,10RS)-8,9-bis(methoxymethoxy)-6,10-dimethyl-2-pivaloyloxyspiro<4.5>dec-6-ene 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: 91.0%

formaldehyde ethyl methyl acetal (22251-34-9) + (2RS,5RS,8SR,9SR,10RS)-9-methoxymethoxy-6,10-dimethyl-2-pivaloyloxyspiro<4.5>dec-6-en-8-ol (101415-98-9,101470-77-3) → (2RS,5RS,8SR,9SR,10RS)-8,9-bis(methoxymethoxy)-6,10-dimethyl-2-pivaloyloxyspiro<4.5>dec-6-ene (101467-36-1)

Guidance literature:

DOI:10.1016/S0040-4039(00)98159-0

Reference yield:

(2RS,5RS,8SR,9SR,10RS)-8,9-bis(methoxymethoxy)-6,10-dimethyl-2-pivaloyloxyspiro<4.5>dec-6-ene (101467-36-1) → (+/-)-oxylubimin (55784-90-2,69350-60-3,74644-54-5,83113-69-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 95 percent / MeLi / diethyl ether / 0.08 h / 0 °C

2: pyridine / 12 h / 0 °C

3: 1) NaH / 1) DME, 0 deg C, 2) DME, 7h, reflux

4: 1) NaH, 2) Red-Al / 1) DME, RT, 30 min, 2) DME, toluene, 30 min, reflux

5: 78 percent / NaBH₄, CoCl₂*6H₂O / ethanol / 24 h / Ambient temperature

6: 79 percent / pyridine / 2 h / 0 °C

7: 82 percent / SeO₂, CaCO₃ / xylene / 0.67 h / Heating

8: 88 percent / NaBH₄ / methanol / 0.17 h / 0 °C

9: 90 percent / H₂ / Raney Ni(W₂) / ethanol / 2 h / 760 Torr / Ambient temperature

10: 82 percent / PCC, NaOAc / CH₂Cl₂ / 2 h / Ambient temperature

11: 68 percent / 3N HCl / tetrahydrofuran / 6 h / Ambient temperature

12: 1) NaI, 2) DBU / 1) DME RT, 2) reflux

With pyridine; hydrogenchloride; sodium tetrahydroborate; selenium(IV) oxide; methyllithium; hydrogen; sodium acetate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; calcium carbonate; sodium iodide; cobalt(II) chloride; Raney Ni(W₂); In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; xylene;

DOI:10.1248/cpb.38.361

Reference yield:

(2RS,5RS,8SR,9SR,10RS)-8,9-bis(methoxymethoxy)-6,10-dimethyl-2-pivaloyloxyspiro<4.5>dec-6-ene (101467-36-1) → (+/-)-10-epioxylubimin (55784-90-2,69350-60-3,74644-54-5,83113-69-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 95 percent / MeLi / diethyl ether / 0.08 h / 0 °C

2: pyridine / 12 h / 0 °C

3: 1) NaH / 1) DME, 0 deg C, 2) DME, 7h, reflux

4: 1) NaH, 2) Red-Al / 1) DME, RT, 30 min, 2) DME, toluene, 30 min, reflux

5: 78 percent / NaBH₄, CoCl₂*6H₂O / ethanol / 24 h / Ambient temperature

6: 79 percent / pyridine / 2 h / 0 °C

7: 82 percent / SeO₂, CaCO₃ / xylene / 0.67 h / Heating

8: 88 percent / NaBH₄ / methanol / 0.17 h / 0 °C

9: 90 percent / H₂ / Raney Ni(W₂) / ethanol / 2 h / 760 Torr / Ambient temperature

10: 82 percent / PCC, NaOAc / CH₂Cl₂ / 2 h / Ambient temperature

11: 68 percent / 3N HCl / tetrahydrofuran / 6 h / Ambient temperature

12: 1) NaI, 2) DBU / 1) DME RT, 2) reflux

With pyridine; hydrogenchloride; sodium tetrahydroborate; selenium(IV) oxide; methyllithium; hydrogen; sodium acetate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; calcium carbonate; sodium iodide; cobalt(II) chloride; Raney Ni(W₂); In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; xylene;

DOI:10.1248/cpb.38.361

upstream raw materials:

formaldehyde ethyl methyl acetal

(2RS,5RS,8SR,9SR,10RS)-9-methoxymethoxy-6,10-dimethyl-2-pivaloyloxyspiro<4.5>dec-6-en-8-ol

Downstream raw materials:

(+/-)-10-epioxylubimin

(+/-)-oxylubimin

Refernces