(3R,4R,5S,6S,8S,9S)-4-Methoxy-6-(4-methoxy-benzyloxy)-8-methoxymethoxy-3,5,9-trimethyl-undeca-1,10-dien-3-ol

Base Information

• Chemical Name: (3R,4R,5S,6S,8S,9S)-4-Methoxy-6-(4-methoxy-benzyloxy)-8-methoxymethoxy-3,5,9-trimethyl-undeca-1,10-dien-3-ol
• CAS No.: 177598-69-5
• Molecular Formula: C₂₅H₄₀O₆
• Molecular Weight: 436.589
• Mol file: 177598-69-5.mol

Synonyms:

Chemical Property of (3R,4R,5S,6S,8S,9S)-4-Methoxy-6-(4-methoxy-benzyloxy)-8-methoxymethoxy-3,5,9-trimethyl-undeca-1,10-dien-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5S,6S,8S,9S)-4-Methoxy-6-(4-methoxy-benzyloxy)-8-methoxymethoxy-3,5,9-trimethyl-undeca-1,10-dien-3-ol

There total 12 articles about (3R,4R,5S,6S,8S,9S)-4-Methoxy-6-(4-methoxy-benzyloxy)-8-methoxymethoxy-3,5,9-trimethyl-undeca-1,10-dien-3-ol 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:

(2R,3R,4S)-2-(Benzyloxy)-4-methyl-5-hexen-3-ol (124377-76-0) → (3R,4R,5S,6S,8S,9S)-4-Methoxy-6-(4-methoxy-benzyloxy)-8-methoxymethoxy-3,5,9-trimethyl-undeca-1,10-dien-3-ol (177598-69-5)

Guidance literature:

Multi-step reaction with 12 steps

1: KH

2: Li, NH₃

4: 1.) OsO₄, NMO, 2.) Pb(OAc)4

5: 1.) TiCl₄ / 1.) -78 deg C, 10 min

6: 1.) KH

7: 1.) OsO₄, NMO, 2.) Pb(OAc)4

8: BF₃*Et₂O

9: diisopropyl ethyl amine

10: TBAF

11: PCC

12: tetrahydrofuran

With lead(IV) acetate; osmium(VIII) oxide; N-methyl-2-indolinone; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; ammonia; titanium tetrachloride; lithium; potassium hydride; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran;

DOI:10.1016/0040-4039(96)00578-3

Reference yield:

(2R,3R,4S)-3-methoxy-4-methylhex-5-en-2-ol → (3R,4R,5S,6S,8S,9S)-4-Methoxy-6-(4-methoxy-benzyloxy)-8-methoxymethoxy-3,5,9-trimethyl-undeca-1,10-dien-3-ol (177598-69-5)

Guidance literature:

Multi-step reaction with 10 steps

2: 1.) OsO₄, NMO, 2.) Pb(OAc)4

3: 1.) TiCl₄ / 1.) -78 deg C, 10 min

4: 1.) KH

5: 1.) OsO₄, NMO, 2.) Pb(OAc)4

6: BF₃*Et₂O

7: diisopropyl ethyl amine

8: TBAF

9: PCC

10: tetrahydrofuran

With lead(IV) acetate; osmium(VIII) oxide; N-methyl-2-indolinone; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; titanium tetrachloride; potassium hydride; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran;

DOI:10.1016/0040-4039(96)00578-3

Reference yield:

tert-butyl((2R,3R,4S)-3-methoxy-4-methylhex-5-en-2-yloxy)dimethylsilane (177598-64-0) → (3R,4R,5S,6S,8S,9S)-4-Methoxy-6-(4-methoxy-benzyloxy)-8-methoxymethoxy-3,5,9-trimethyl-undeca-1,10-dien-3-ol (177598-69-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) OsO₄, NMO, 2.) Pb(OAc)4

2: 1.) TiCl₄ / 1.) -78 deg C, 10 min

3: 1.) KH

4: 1.) OsO₄, NMO, 2.) Pb(OAc)4

5: BF₃*Et₂O

6: diisopropyl ethyl amine

7: TBAF

8: PCC

9: tetrahydrofuran

With lead(IV) acetate; osmium(VIII) oxide; N-methyl-2-indolinone; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; titanium tetrachloride; potassium hydride; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran;

DOI:10.1016/0040-4039(96)00578-3

upstream raw materials:

vinyl magnesium bromide

(3R,4S,5S,7S,8S)-3-Methoxy-5-(4-methoxy-benzyloxy)-7-methoxymethoxy-4,8-dimethyl-dec-9-en-2-one

(2R,3R,4S)-2-(Benzyloxy)-4-methyl-5-hexen-3-ol

tert-butyl((2R,3R,4S)-3-methoxy-4-methylhex-5-en-2-yloxy)dimethylsilane

Downstream raw materials:

4-[(1E,3E,5E)-(7R,8S,9S,11S,12S)-4-Benzenesulfonyl-7-methoxy-9-(4-methoxy-benzyloxy)-11-methoxymethoxy-2,6,8,12-tetramethyl-tetradeca-1,3,5,13-tetraenyl]-2-methyl-oxazole

1-[(E)-(1S,2S,3R)-6-Benzenesulfonyl-3-methoxy-1-((2S,3S)-2-methoxymethoxy-3-methyl-pent-4-enyl)-2,4-dimethyl-hex-4-enyloxymethyl]-4-methoxy-benzene