(4S,5R,E)-methyl 5-((5aR,7S,8S,9aR)-8-hydroxy-2,2-dimethylhexahydro-4H-pyrano[3,2-d][1,3]dioxepin-7-yl)-4-(4-methoxybenzyloxy)hex-2-enoate

Base Information

• Chemical Name: (4S,5R,E)-methyl 5-((5aR,7S,8S,9aR)-8-hydroxy-2,2-dimethylhexahydro-4H-pyrano[3,2-d][1,3]dioxepin-7-yl)-4-(4-methoxybenzyloxy)hex-2-enoate
• CAS No.: 142325-62-0
• Molecular Formula: C₂₅H₃₆O₈
• Molecular Weight: 464.556
• Mol file: 142325-62-0.mol

Synonyms:(4S,5R,E)-methyl 5-((5aR,7S,8S,9aR)-8-hydroxy-2,2-dimethylhexahydro-4H-pyrano[3,2-d][1,3]dioxepin-7-yl)-4-(4-methoxybenzyloxy)hex-2-enoate

Chemical Property of (4S,5R,E)-methyl 5-((5aR,7S,8S,9aR)-8-hydroxy-2,2-dimethylhexahydro-4H-pyrano[3,2-d][1,3]dioxepin-7-yl)-4-(4-methoxybenzyloxy)hex-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R,E)-methyl 5-((5aR,7S,8S,9aR)-8-hydroxy-2,2-dimethylhexahydro-4H-pyrano[3,2-d][1,3]dioxepin-7-yl)-4-(4-methoxybenzyloxy)hex-2-enoate

There total 6 articles about (4S,5R,E)-methyl 5-((5aR,7S,8S,9aR)-8-hydroxy-2,2-dimethylhexahydro-4H-pyrano[3,2-d][1,3]dioxepin-7-yl)-4-(4-methoxybenzyloxy)hex-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:

(E)-(4S,5R)-5-[(2S,3S,5R,6R)-3,5-Dihydroxy-6-(2-hydroxy-ethyl)-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-hex-2-enoic acid methyl ester (157322-60-6) + 2,2-dimethoxy-propane (77-76-9) → (4S,5R,E)-methyl 5-((5aR,7S,8S,9aR)-8-hydroxy-2,2-dimethylhexahydro-4H-pyrano[3,2-d][1,3]dioxepin-7-yl)-4-(4-methoxybenzyloxy)hex-2-enoate (142325-62-0)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)91671-X

Reference yield:

(S)-2-((2S,3S,5R,6R)-3,5-bis(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)propanal (142325-59-5) → (4S,5R,E)-methyl 5-((5aR,7S,8S,9aR)-8-hydroxy-2,2-dimethylhexahydro-4H-pyrano[3,2-d][1,3]dioxepin-7-yl)-4-(4-methoxybenzyloxy)hex-2-enoate (142325-62-0)

Guidance literature:

Multi-step reaction with 5 steps

1: NiCl₂/CrCl₂ / tetrahydrofuran / Ambient temperature

3: BF₃*Et₂O / CH₂Cl₂ / 0 °C

4: HF*Py / acetonitrile / Ambient temperature

5: PPTS / CH₂Cl₂ / Ambient temperature

With chromium dichloride; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; pyridine hydrogenfluoride; nickel dichloride; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)91671-X

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (4S,5R,E)-methyl 5-((5aR,7S,8S,9aR)-8-hydroxy-2,2-dimethylhexahydro-4H-pyrano[3,2-d][1,3]dioxepin-7-yl)-4-(4-methoxybenzyloxy)hex-2-enoate (142325-62-0)

Guidance literature:

Multi-step reaction with 3 steps

1: BF₃*Et₂O / CH₂Cl₂ / 0 °C

2: HF*Py / acetonitrile / Ambient temperature

3: PPTS / CH₂Cl₂ / Ambient temperature

With boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; pyridine hydrogenfluoride; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)91671-X

upstream raw materials:

(E)-(4S,5R)-5-[(2S,3S,5R,6R)-3,5-Dihydroxy-6-(2-hydroxy-ethyl)-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-hex-2-enoic acid methyl ester

2,2-dimethoxy-propane

O-(4-methoxybenzyl)-trichloroacetimidate

(S)-2-((2S,3S,5R,6R)-3,5-bis(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)propanal

Downstream raw materials:

[(2S,3R,4R,4aS,5aR,10aR,11aS)-3-(4-Methoxy-benzyloxy)-4,9,9-trimethyl-decahydro-1,5,8,10-tetraoxa-cyclohepta[b]naphthalen-2-yl]-acetic acid methyl ester

methyl 2-((2S,3R,4R,4aS,6R,7R,8aS)-7-(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-3-(4-methoxybenzyloxy)-4-methyloctahydropyrano[3,2-b]pyran-2-yl)acetate

2-((2S,3R,4R,4aS,6R,7R,8aS)-7-(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-3-(4-methoxybenzyloxy)-4-methyloctahydropyrano[3,2-b]pyran-2-yl)ethanol

[(2S,3R,4R,4aS,6R,7R,8aS)-7-Hydroxy-6-(2-hydroxy-ethyl)-3-(4-methoxy-benzyloxy)-4-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid methyl ester