(2R,3S,4R,5R,6S)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol

Base Information

Chemical Name:(2R,3S,4R,5R,6S)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol
CAS No.:140386-69-2
Molecular Formula:C₃₄H₄₄O₈
Molecular Weight:580.719
Hs Code.:

Synonyms:(2R,3S,4R,5R,6S)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol

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Chemical Property of (2R,3S,4R,5R,6S)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol

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Technology Process of (2R,3S,4R,5R,6S)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol

There total 5 articles about (2R,3S,4R,5R,6S)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol 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: 9.0%

: 140201-53-2
(2S,3R,4S,5R)-3,4,5-Tris(benzyloxy)-2,6-bis(methoxymethoxy)hexanal

: 106-95-6
allyl bromide

: 140201-56-5
(2R,3S,4R,5R,6R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol

: 140386-69-2
(2R,3S,4R,5R,6S)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol

Guidance literature:: With chromium chloride; lithium aluminium tetrahydride; In tetrahydrofuran; at -6.5 ℃; for 60h;
DOI:10.1021/jo00037a043

Reference yield:

: 18039-26-4,20787-16-0,20787-21-7,77943-32-9,77943-33-0,89615-43-0,89615-44-1,90899-55-1
2,3,4-tri-O-benzyl-D-xylopyranose

: 140386-69-2
(2R,3S,4R,5R,6S)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / tetrahydrofuran / 48 h / Ambient temperature

2: 82 percent / N-ethyldiisopropylamine / CH₂Cl₂ / 24 h

3: 1.) ozone, 2.) PPh₃ / 1.) CH₂Cl₂, 2.) a) -78 deg C, 1 h, b) r.t., 2h

4: 9 percent / CrCl₃, LiAlH₄ / tetrahydrofuran / 60 h / -6.5 °C

With chromium chloride; lithium aluminium tetrahydride; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00037a043

Reference yield:

: 140201-51-0,140386-66-9
(2R,3S,4S,5R/S)-2,3,4-Tri-O-benzyl-6-heptene-1,2,3,4,5-pentol

: 140386-69-2
(2R,3S,4R,5R,6S)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / N-ethyldiisopropylamine / CH₂Cl₂ / 24 h

2: 1.) ozone, 2.) PPh₃ / 1.) CH₂Cl₂, 2.) a) -78 deg C, 1 h, b) r.t., 2h

3: 9 percent / CrCl₃, LiAlH₄ / tetrahydrofuran / 60 h / -6.5 °C

With chromium chloride; lithium aluminium tetrahydride; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00037a043