methyl (E)-(4S,5R,6S,7S,8S)-7-(benzyloxy)-5-hydroxy-8,9-(isopropylidenedioxy)-2,4,6-trimethylnon-2-enoate

Base Information

• Chemical Name: methyl (E)-(4S,5R,6S,7S,8S)-7-(benzyloxy)-5-hydroxy-8,9-(isopropylidenedioxy)-2,4,6-trimethylnon-2-enoate
• CAS No.: 120040-79-1
• Molecular Formula: C₂₃H₃₄O₆
• Molecular Weight: 406.519
• Mol file: 120040-79-1.mol

Synonyms:methyl (E)-(4S,5R,6S,7S,8S)-7-(benzyloxy)-5-hydroxy-8,9-(isopropylidenedioxy)-2,4,6-trimethylnon-2-enoate

Chemical Property of methyl (E)-(4S,5R,6S,7S,8S)-7-(benzyloxy)-5-hydroxy-8,9-(isopropylidenedioxy)-2,4,6-trimethylnon-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (E)-(4S,5R,6S,7S,8S)-7-(benzyloxy)-5-hydroxy-8,9-(isopropylidenedioxy)-2,4,6-trimethylnon-2-enoate

There total 10 articles about methyl (E)-(4S,5R,6S,7S,8S)-7-(benzyloxy)-5-hydroxy-8,9-(isopropylidenedioxy)-2,4,6-trimethylnon-2-enoate 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: 88.0%

(2S,3R,4S,5S)-5-Benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2,4-dimethyl-pentanal (146518-09-4) + methyl 2-(triphenylphosphoranylidene)propionate (2605-68-7) → (Z)-(4R,5S,6S,7S)-7-Benzyloxy-7-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-2,4,6-trimethyl-hept-2-enoic acid methyl ester + methyl (E)-(4S,5R,6S,7S,8S)-7-(benzyloxy)-5-hydroxy-8,9-(isopropylidenedioxy)-2,4,6-trimethylnon-2-enoate (120040-79-1)

Guidance literature:

In dichloromethane; toluene; at 45 ℃; for 12h;

DOI:10.1021/ja00059a024

Reference yield:

2,3-O-bis-methyl-5,6-O-isopropylidene-L-ascorbic acid (58650-93-4,66421-65-6,128142-57-4) → methyl (E)-(4S,5R,6S,7S,8S)-7-(benzyloxy)-5-hydroxy-8,9-(isopropylidenedioxy)-2,4,6-trimethylnon-2-enoate (120040-79-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂

2: LiAlH₄ / tetrahydrofuran

3: Pb(OAc)4

4: 1.) 4 Angstroem molecular sieves / 1.) toluene, 30 min, 2.) toluene, a) -78 deg C, 2 h, b) RT, 15 h

5: 89 percent / NaH / dimethylformamide / 2 h / Ambient temperature

6: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C, 30 min, 2.) MeOH, RT

7: 1.) 4 Angstroem molecular sieves, 3.) NaBH₄

8: 1.) O₃, 2.) Ph₃P / 1.) MeOH, -78 deg C, 2.) MeOH, RT, 2 h

9: 88 percent / toluene; CH₂Cl₂ / 12 h / 45 °C

With lead(IV) acetate; sodium tetrahydroborate; lithium aluminium tetrahydride; dimethylsulfide; 4 A molecular sieve; sodium hydride; ozone; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00059a024

Reference yield:

(2S,3R)-1,2-isopropylidenedioxy-butan-3,4-diol (114185-09-0) → methyl (E)-(4S,5R,6S,7S,8S)-7-(benzyloxy)-5-hydroxy-8,9-(isopropylidenedioxy)-2,4,6-trimethylnon-2-enoate (120040-79-1)

Guidance literature:

Multi-step reaction with 7 steps

1: Pb(OAc)4

2: 1.) 4 Angstroem molecular sieves / 1.) toluene, 30 min, 2.) toluene, a) -78 deg C, 2 h, b) RT, 15 h

3: 89 percent / NaH / dimethylformamide / 2 h / Ambient temperature

4: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C, 30 min, 2.) MeOH, RT

5: 1.) 4 Angstroem molecular sieves, 3.) NaBH₄

6: 1.) O₃, 2.) Ph₃P / 1.) MeOH, -78 deg C, 2.) MeOH, RT, 2 h

7: 88 percent / toluene; CH₂Cl₂ / 12 h / 45 °C

With lead(IV) acetate; sodium tetrahydroborate; dimethylsulfide; 4 A molecular sieve; sodium hydride; ozone; triphenylphosphine; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00059a024

upstream raw materials:

(1S,2S,3S,4R)-1-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4-dimethyl-hex-5-en-3-ol

methyl 2-(triphenylphosphoranylidene)propionate

(2S,3R,4S,5S)-5-Benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2,4-dimethyl-pentanal

2,3-O-bis-methyl-5,6-O-isopropylidene-L-ascorbic acid

Downstream raw materials:

(E)-(4R,5S,6S,7S)-5-Acetoxy-7-benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4,6-trimethyl-hept-2-enoic acid methyl ester

(1S,2S,4aS,5R,6R,7S,8R,8aR)-5-Benzyloxy-2-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propenyl]-7-(imidazole-1-carbothioyloxy)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

(1S,2S,4aS,5R,6R,7S,8R,8aR)-7-Acetoxy-5-benzyloxy-2-((E)-3-hydroxy-1-methyl-propenyl)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

methyl 2β-<(E)-3-hydroxy-1-methylprop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate