(4S,5R,E)-methyl 5-((2S,3S,5R,6R)-3,5-bis(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-4-(4-methoxybenzyloxy)hex-2-enoate

Base Information

• Chemical Name: (4S,5R,E)-methyl 5-((2S,3S,5R,6R)-3,5-bis(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-4-(4-methoxybenzyloxy)hex-2-enoate
• CAS No.: 157322-59-3
• Molecular Formula: C₄₀H₇₄O₈Si₃
• Molecular Weight: 767.279

Synonyms:(4S,5R,E)-methyl 5-((2S,3S,5R,6R)-3,5-bis(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-4-(4-methoxybenzyloxy)hex-2-enoate

Chemical Property of (4S,5R,E)-methyl 5-((2S,3S,5R,6R)-3,5-bis(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)tetrahydro-2H-pyran-2-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-((2S,3S,5R,6R)-3,5-bis(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-4-(4-methoxybenzyloxy)hex-2-enoate

There total 3 articles about (4S,5R,E)-methyl 5-((2S,3S,5R,6R)-3,5-bis(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)tetrahydro-2H-pyran-2-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: 95.0%

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) + (4S,5R,E)-methyl 5-((2S,3S,5R,6R)-3,5-bis(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-4-hydroxyhex-2-enoate (142325-61-9) → (4S,5R,E)-methyl 5-((2S,3S,5R,6R)-3,5-bis(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-4-(4-methoxybenzyloxy)hex-2-enoate (157322-59-3)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ol702559e

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-((2S,3S,5R,6R)-3,5-bis(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-4-(4-methoxybenzyloxy)hex-2-enoate (157322-59-3)

Guidance literature:

Multi-step reaction with 3 steps

1: NiCl₂/CrCl₂ / tetrahydrofuran / Ambient temperature

3: BF₃*Et₂O / CH₂Cl₂ / 0 °C

With chromium dichloride; boron trifluoride diethyl etherate; nickel dichloride; In tetrahydrofuran; dichloromethane;

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

Reference yield:

(4R,5R,E)-methyl 5-((2S,3S,5R,6R)-3,5-bis(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-4-hydroxyhex-2-enoate (142325-60-8) → (4S,5R,E)-methyl 5-((2S,3S,5R,6R)-3,5-bis(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-4-(4-methoxybenzyloxy)hex-2-enoate (157322-59-3)

Guidance literature:

Multi-step reaction with 2 steps

2: BF₃*Et₂O / CH₂Cl₂ / 0 °C

With boron trifluoride diethyl etherate; In dichloromethane;

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

upstream raw materials:

O-(4-methoxybenzyl)-trichloroacetimidate

(4S,5R,E)-methyl 5-((2S,3S,5R,6R)-3,5-bis(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-4-hydroxyhex-2-enoate

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

(4R,5R,E)-methyl 5-((2S,3S,5R,6R)-3,5-bis(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-4-hydroxyhex-2-enoate

Downstream 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

[(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

[(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

(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

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