(Z)-7-Benzyloxy-3-[(R)-3-(2-methoxy-ethoxymethoxy)-2-methyl-propyl]-hept-2-enoic acid methyl ester

Base Information

• Chemical Name: (Z)-7-Benzyloxy-3-[(R)-3-(2-methoxy-ethoxymethoxy)-2-methyl-propyl]-hept-2-enoic acid methyl ester
• CAS No.: 119243-78-6
• Molecular Formula: C₂₃H₃₆O₆
• Molecular Weight: 408.535
• Mol file: 119243-78-6.mol

Synonyms:(Z)-7-Benzyloxy-3-[(R)-3-(2-methoxy-ethoxymethoxy)-2-methyl-propyl]-hept-2-enoic acid methyl ester

Chemical Property of (Z)-7-Benzyloxy-3-[(R)-3-(2-methoxy-ethoxymethoxy)-2-methyl-propyl]-hept-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-7-Benzyloxy-3-[(R)-3-(2-methoxy-ethoxymethoxy)-2-methyl-propyl]-hept-2-enoic acid methyl ester

There total 2 articles about (Z)-7-Benzyloxy-3-[(R)-3-(2-methoxy-ethoxymethoxy)-2-methyl-propyl]-hept-2-enoic acid methyl ester 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:

(R)-5-(2-Methoxy-ethoxymethoxy)-4-methyl-pent-1-yne (119243-76-4) → (Z)-7-Benzyloxy-3-[(R)-3-(2-methoxy-ethoxymethoxy)-2-methyl-propyl]-hept-2-enoic acid methyl ester (119243-78-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) THF, -78 -> 78 deg C, 2.) -78 deg C

2: 1.) DMS*CuBr, TMEDA / 1.) Et₂O, -78 deg C, 2.) -78 deg C

With n-butyllithium; copper(I) bromide dimethylsulfide complex; N,N,N,N,-tetramethylethylenediamine;

DOI:10.1021/ja00187a081

Reference yield:

(4-Benzyloxy)butylmagnesium bromide + (R)-6-(2-Methoxy-ethoxymethoxy)-5-methyl-hex-2-ynoic acid methyl ester (119243-77-5) → (Z)-7-Benzyloxy-3-[(R)-3-(2-methoxy-ethoxymethoxy)-2-methyl-propyl]-hept-2-enoic acid methyl ester (119243-78-6) + (E)-7-Benzyloxy-3-[(R)-3-(2-methoxy-ethoxymethoxy)-2-methyl-propyl]-hept-2-enoic acid methyl ester (119243-95-7)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; N,N,N,N,-tetramethylethylenediamine; Yield given. Multistep reaction. Yields of byproduct given; 1.) Et₂O, -78 deg C, 2.) -78 deg C;

DOI:10.1021/ja00187a081

Reference yield:

(Z)-7-Benzyloxy-3-[(R)-3-(2-methoxy-ethoxymethoxy)-2-methyl-propyl]-hept-2-enoic acid methyl ester (119243-78-6) → (Z)-(2S,8S)-8-Azido-8-[(2S,4R)-2-(4-benzyloxy-butyl)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-oct-4-enoic acid methyl ester (119243-90-2)

Guidance literature:

Multi-step reaction with 14 steps

1: 98 percent / DIBAL / CH₂Cl₂ / -78 °C

2: Ti(O-iPr)4, D-DIPT, t-BuOOH, 4-Angstroem sieves / CH₂Cl₂ / -50 °C

3: ClCOCOCl, DMSO, Et₃N / CH₂Cl₂ / -78 - 0 °C

4: 89 percent / CH₂Cl₂

5: 1.) LiBH₄, MeOH, 2.) H₂ / 2.) 5percent Rh/Al₂O₃ / 1.) Et₂O, 0 deg C, 2.) THF, 1 atm

6: 97 percent / Et₃N / CH₂Cl₂

7: 94 percent / LiN₃, DMPU / 110 °C

8: 81 percent / BF₃*Et₂O / CH₂Cl₂ / 0 °C

9: 97 percent / LiOH / tetrahydrofuran; methanol; H₂O

10: 91 percent / ClCOCOCl, DMSO, Et₃N / CH₂Cl₂ / -78 - 0 °C

11: 81 percent / KO-t-Bu / tetrahydrofuran / -10 °C

12: 72 percent / aq. HBF₄ / methanol / 0.5 h

13: 86 percent / LiOH / tetrahydrofuran; methanol; H₂O / 22 °C

14: 1.) Jones' reagent, Celite / 1.) THF, 0 deg C, 2.) ether

With titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; lithium borohydride; tetrafluoroboric acid; jones' reagent; lithium azide; oxalyl dichloride; 4 A molecular sieve; Celite; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; Rh/Al₂O₃; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ja00187a081

upstream raw materials:

(R)-6-(2-Methoxy-ethoxymethoxy)-5-methyl-hex-2-ynoic acid methyl ester

(R)-5-(2-Methoxy-ethoxymethoxy)-4-methyl-pent-1-yne

Downstream raw materials:

croomine

(2R,4R)-2-(4-Benzyloxy-butyl)-4-methyl-tetrahydro-furan-2-carbaldehyde

(E)-4-[(2R,4R)-2-(4-Benzyloxy-butyl)-4-methyl-tetrahydro-furan-2-yl]-4-oxo-but-2-enoic acid methyl ester

(S)-4-Azido-4-[(4S,6R)-4-(4-benzyloxy-butyl)-6-methyl-[1,3]dioxepan-4-yl]-butan-1-ol