8(R)-<(tert-butoxycarbonyl)methyl>-2(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3(R),5(R),9(R)-trimethyl-(6R)-1,7-dioxaspiro<5.5>undecane

Base Information

• Chemical Name: 8(R)-<(tert-butoxycarbonyl)methyl>-2(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3(R),5(R),9(R)-trimethyl-(6R)-1,7-dioxaspiro<5.5>undecane
• CAS No.: 122213-44-9
• Molecular Formula: C₃₇H₅₆O₅Si
• Molecular Weight: 608.934

Synonyms:

Chemical Property of 8(R)-<(tert-butoxycarbonyl)methyl>-2(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3(R),5(R),9(R)-trimethyl-(6R)-1,7-dioxaspiro<5.5>undecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8(R)-<(tert-butoxycarbonyl)methyl>-2(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3(R),5(R),9(R)-trimethyl-(6R)-1,7-dioxaspiro<5.5>undecane

There total 19 articles about 8(R)-<(tert-butoxycarbonyl)methyl>-2(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3(R),5(R),9(R)-trimethyl-(6R)-1,7-dioxaspiro<5.5>undecane 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:

(E)-(R)-7-Bromo-2,5-dimethyl-hept-3-ene (122213-32-5) → 8(R)-<(tert-butoxycarbonyl)methyl>-2(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3(R),5(R),9(R)-trimethyl-(6R)-1,7-dioxaspiro<5.5>undecane (122213-44-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 48 percent / dimethylformamide / Ambient temperature

2: 1.) n-BuLi / 1.) THF, -78 deg C, 45 min, 2.) a) THF, -78 deg C, 50 min, b) 0 deg C, 30 min

3: oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

4: 74 mg / disodium hydrogen phosphate, Na/Hg / methanol / 2.5 h / 0 °C

5: 1.) O₃, NaHCO₃, 2.) dimethyl sulfide / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) a) -78 deg C, 10 min, b) RT, 1.5 h

6: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 5 min

7: 78 percent / p-TsOH / methanol / 1.) 0 deg C, 2 h, 2.) RT, 6 h

8: 93 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 18 h / 25 °C

9: pyridine / CH₂Cl₂ / 5 h / 25 °C

10: 1.) tri-n-butyltin hydride, AIBN, 2.) I₂ / 1.) toluene, reflux, 2 h, 2.) CH₂Cl₂

With pyridine; dmap; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; oxalyl dichloride; dimethylsulfide; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00275a019

Reference yield:

(E)-(R)-3,6-Dimethyl-hept-4-en-1-ol (122213-31-4) → 8(R)-<(tert-butoxycarbonyl)methyl>-2(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3(R),5(R),9(R)-trimethyl-(6R)-1,7-dioxaspiro<5.5>undecane (122213-44-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) triethylamine, methanesulfonyl chloride, 2.) LiBr / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) acetone, reflux

2: 48 percent / dimethylformamide / Ambient temperature

3: 1.) n-BuLi / 1.) THF, -78 deg C, 45 min, 2.) a) THF, -78 deg C, 50 min, b) 0 deg C, 30 min

4: oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

5: 74 mg / disodium hydrogen phosphate, Na/Hg / methanol / 2.5 h / 0 °C

6: 1.) O₃, NaHCO₃, 2.) dimethyl sulfide / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) a) -78 deg C, 10 min, b) RT, 1.5 h

7: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 5 min

8: 78 percent / p-TsOH / methanol / 1.) 0 deg C, 2 h, 2.) RT, 6 h

9: 93 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 18 h / 25 °C

10: pyridine / CH₂Cl₂ / 5 h / 25 °C

11: 1.) tri-n-butyltin hydride, AIBN, 2.) I₂ / 1.) toluene, reflux, 2 h, 2.) CH₂Cl₂

With pyridine; dmap; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; oxalyl dichloride; dimethylsulfide; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; lithium bromide; lithium diisopropyl amide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00275a019

Reference yield:

(E)-(R)-3,6-Dimethyl-hept-4-enoic acid methyl ester (122213-30-3) → 8(R)-<(tert-butoxycarbonyl)methyl>-2(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3(R),5(R),9(R)-trimethyl-(6R)-1,7-dioxaspiro<5.5>undecane (122213-44-9)

Guidance literature:

Multi-step reaction with 12 steps

1: LiAlH₄ / diethyl ether / Ambient temperature

2: 1.) triethylamine, methanesulfonyl chloride, 2.) LiBr / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) acetone, reflux

3: 48 percent / dimethylformamide / Ambient temperature

4: 1.) n-BuLi / 1.) THF, -78 deg C, 45 min, 2.) a) THF, -78 deg C, 50 min, b) 0 deg C, 30 min

5: oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

6: 74 mg / disodium hydrogen phosphate, Na/Hg / methanol / 2.5 h / 0 °C

7: 1.) O₃, NaHCO₃, 2.) dimethyl sulfide / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) a) -78 deg C, 10 min, b) RT, 1.5 h

8: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 5 min

9: 78 percent / p-TsOH / methanol / 1.) 0 deg C, 2 h, 2.) RT, 6 h

10: 93 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 18 h / 25 °C

11: pyridine / CH₂Cl₂ / 5 h / 25 °C

12: 1.) tri-n-butyltin hydride, AIBN, 2.) I₂ / 1.) toluene, reflux, 2 h, 2.) CH₂Cl₂

With pyridine; dmap; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethylsulfide; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; lithium bromide; lithium diisopropyl amide; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00275a019

upstream raw materials:

{(2R,3R,6S,8R,9S,10S,11R)-8-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3,9,11-trimethyl-10-phenoxythiocarbonyloxy-1,7-dioxa-spiro[5.5]undec-2-yl}-acetic acid tert-butyl ester

(E)-(R)-7-Bromo-2,5-dimethyl-hept-3-ene

(E)-(R)-3,6-Dimethyl-hept-4-en-1-ol

(E)-(R)-3,6-Dimethyl-hept-4-enoic acid methyl ester

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