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

Base Information

Chemical Name:4(S)-hydroxy-8(S)-<(tert-butoxycarbonyl)methyl>-2(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3(R),5(R),9(R)-trimethyl-(6S)-1,7-dioxaspiro<5.5>undecane
CAS No.:122213-42-7
Molecular Formula:C₃₇H₅₆O₆Si
Molecular Weight:624.934
Hs Code.:

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

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Chemical Property of 4(S)-hydroxy-8(S)-<(tert-butoxycarbonyl)methyl>-2(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3(R),5(R),9(R)-trimethyl-(6S)-1,7-dioxaspiro<5.5>undecane

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Technology Process of 4(S)-hydroxy-8(S)-<(tert-butoxycarbonyl)methyl>-2(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3(R),5(R),9(R)-trimethyl-(6S)-1,7-dioxaspiro<5.5>undecane

There total 27 articles about 4(S)-hydroxy-8(S)-<(tert-butoxycarbonyl)methyl>-2(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3(R),5(R),9(R)-trimethyl-(6S)-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: 93.0%

: 122213-40-5
4(S)-hydroxy-8(R)-<(tert-butoxycarbonyl)methyl>-2(R)-<1(R)-methyl-2-hydroxyethyl>-3(R),5(R),9(R)-trimethyl-6(R)-1,7-dioxaspiro<5.5>undecane

: 58479-61-1
tert-butylchlorodiphenylsilane

: 122213-42-7,122330-51-2
4(S)-hydroxy-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

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 25 ℃; for 18h;
DOI:10.1021/jo00275a019

Reference yield: 56.0%

: 122213-39-2
hemiketal of 6(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-4(S)-<7-(tert-butoxycarbonyl)-1(R),5(R)-dimethyl-6(S)-hydroxy-2-oxoheptanyl>-2,2,5(S)-trimethyl-1,3-dioxane

: 122213-42-7,122330-51-2
4(S)-hydroxy-8(S)-<(tert-butoxycarbonyl)methyl>-2(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3(R),5(R),9(R)-trimethyl-(6S)-1,7-dioxaspiro<5.5>undecane

Guidance literature:: With toluene-4-sulfonic acid; In methanol; 1.) 0 deg C, 1 h, 2.) RT, 1 h;
DOI:10.1021/jo00275a019

Reference yield:

: 122213-32-5
(E)-(R)-7-Bromo-2,5-dimethyl-hept-3-ene

: 122213-42-7,122330-51-2
4(S)-hydroxy-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

Guidance literature:: Multi-step reaction with 8 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

With dmap; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; oxalyl dichloride; dimethylsulfide; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00275a019