(4R,5R)-methyl 5-{(1E,3R,7S,9E,11R,12S,13R,14R)-12-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-14-methoxy-16-[(4-methoxybenzyl)oxy]-3,7,9,11,13-pentamethylhexadeca-1,9-dienyl}-2,2-dimethyl-1,3-dioxalone-4-carboxylate

Base Information

• Chemical Name: (4R,5R)-methyl 5-{(1E,3R,7S,9E,11R,12S,13R,14R)-12-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-14-methoxy-16-[(4-methoxybenzyl)oxy]-3,7,9,11,13-pentamethylhexadeca-1,9-dienyl}-2,2-dimethyl-1,3-dioxalone-4-carboxylate
• CAS No.: 1427556-65-7
• Molecular Formula: C₄₃H₇₄O₉Si
• Molecular Weight: 763.141
• Mol file: 1427556-65-7.mol

Synonyms:

Chemical Property of (4R,5R)-methyl 5-{(1E,3R,7S,9E,11R,12S,13R,14R)-12-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-14-methoxy-16-[(4-methoxybenzyl)oxy]-3,7,9,11,13-pentamethylhexadeca-1,9-dienyl}-2,2-dimethyl-1,3-dioxalone-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-methyl 5-{(1E,3R,7S,9E,11R,12S,13R,14R)-12-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-14-methoxy-16-[(4-methoxybenzyl)oxy]-3,7,9,11,13-pentamethylhexadeca-1,9-dienyl}-2,2-dimethyl-1,3-dioxalone-4-carboxylate

There total 17 articles about (4R,5R)-methyl 5-{(1E,3R,7S,9E,11R,12S,13R,14R)-12-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-14-methoxy-16-[(4-methoxybenzyl)oxy]-3,7,9,11,13-pentamethylhexadeca-1,9-dienyl}-2,2-dimethyl-1,3-dioxalone-4-carboxylate 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:

(4R,5R)-methyl 5-((3R,7S,E)-3,7-dimethyl-8-oxooct-1-en-1-yl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate + tert-butyl{[(4R,5S,6R,7R,1E)-2-iodo-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-en-5-yl]oxy}dimethylsilane (1427556-42-0) → (4R,5R)-methyl 5-{(1E,3R,7S,9E,11R,12S,13R,14R)-12-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-14-methoxy-16-[(4-methoxybenzyl)oxy]-3,7,9,11,13-pentamethylhexadeca-1,9-dienyl}-2,2-dimethyl-1,3-dioxalone-4-carboxylate (1427556-65-7) + (4R,5R)-methyl 5-{(1E,3R,7S,9E,11R,12S,13R,14R)-12-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-14-methoxy-16-[(4-methoxybenzyl)oxy]-3,7,9,11,13-pentamethylhexadeca-1,9-dienyl}-2,2-dimethyl-1,3-dioxalone-4-carboxylate (1427556-63-5)

Guidance literature:

(4R,5R)-methyl 5-((3R,7S,E)-3,7-dimethyl-8-oxooct-1-en-1-yl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate; With chromium dichloride; nickel dichloride; In dimethyl sulfoxide; at 20 ℃; for 0.166667h; Inert atmosphere;

tert-butyl{[(4R,5S,6R,7R,1E)-2-iodo-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-en-5-yl]oxy}dimethylsilane; In dimethyl sulfoxide; at 20 ℃; for 10h; Overall yield = 31 %; Overall yield = 38 mg; Optical yield = 20 %de; Inert atmosphere;

DOI:10.1055/s-0032-1317700

Reference yield:

(4R,5R)-2,2-Dimethyl-5-vinyl-1,3-dioxolan-4-carbonsaeure-methylester (85963-83-3) → (4R,5R)-methyl 5-{(1E,3R,7S,9E,11R,12S,13R,14R)-12-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-14-methoxy-16-[(4-methoxybenzyl)oxy]-3,7,9,11,13-pentamethylhexadeca-1,9-dienyl}-2,2-dimethyl-1,3-dioxalone-4-carboxylate (1427556-65-7) + (4R,5R)-methyl 5-{(1E,3R,7S,9E,11R,12S,13R,14R)-12-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-14-methoxy-16-[(4-methoxybenzyl)oxy]-3,7,9,11,13-pentamethylhexadeca-1,9-dienyl}-2,2-dimethyl-1,3-dioxalone-4-carboxylate (1427556-63-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 10 h / 27 °C / Inert atmosphere

2.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1 h / 0 °C / Inert atmosphere

3.1: chromium dichloride; nickel dichloride / dimethyl sulfoxide / 0.17 h / 20 °C / Inert atmosphere

3.2: 10 h / 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; chromium dichloride; sodium hydrogencarbonate; Dess-Martin periodane; nickel dichloride; In dichloromethane; dimethyl sulfoxide; 1.1: |Cross Metathesis;

DOI:10.1055/s-0032-1317700

Reference yield:

(4R,5R)-methyl 5-[(3R,7S,E)-8-hydroxy-3,7-dimethyloct-1-en-1-yl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate (1360572-00-4) → (4R,5R)-methyl 5-{(1E,3R,7S,9E,11R,12S,13R,14R)-12-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-14-methoxy-16-[(4-methoxybenzyl)oxy]-3,7,9,11,13-pentamethylhexadeca-1,9-dienyl}-2,2-dimethyl-1,3-dioxalone-4-carboxylate (1427556-65-7) + (4R,5R)-methyl 5-{(1E,3R,7S,9E,11R,12S,13R,14R)-12-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-14-methoxy-16-[(4-methoxybenzyl)oxy]-3,7,9,11,13-pentamethylhexadeca-1,9-dienyl}-2,2-dimethyl-1,3-dioxalone-4-carboxylate (1427556-63-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1 h / 0 °C / Inert atmosphere

2.1: chromium dichloride; nickel dichloride / dimethyl sulfoxide / 0.17 h / 20 °C / Inert atmosphere

2.2: 10 h / 20 °C / Inert atmosphere

With chromium dichloride; sodium hydrogencarbonate; Dess-Martin periodane; nickel dichloride; In dichloromethane; dimethyl sulfoxide;

DOI:10.1055/s-0032-1317700

upstream raw materials:

tert-butyl{[(4R,5S,6R,7R,1E)-2-iodo-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-en-5-yl]oxy}dimethylsilane

(R)-2,2-dimethyl-3-(3-methylpent-4-en-1-yl)oxirane

(R,E)-ethyl 6-methylocta-2,7-dienoate

(R)-methyl 6-methyloct-7-enoate