3-O-(4-Methoxybenzyl)-4-[(3S,4R,1E)-4-benzyloxymethoxy-3-hydroxypent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose

Base Information

Chemical Name:3-O-(4-Methoxybenzyl)-4-[(3S,4R,1E)-4-benzyloxymethoxy-3-hydroxypent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose
CAS No.:154674-71-2
Molecular Formula:C₂₈H₃₆O₈
Molecular Weight:500.589
Hs Code.:

Synonyms:3-O-(4-Methoxybenzyl)-4-[(3S,4R,1E)-4-benzyloxymethoxy-3-hydroxypent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose

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Chemical Property of 3-O-(4-Methoxybenzyl)-4-[(3S,4R,1E)-4-benzyloxymethoxy-3-hydroxypent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose

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Technology Process of 3-O-(4-Methoxybenzyl)-4-[(3S,4R,1E)-4-benzyloxymethoxy-3-hydroxypent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose

There total 10 articles about 3-O-(4-Methoxybenzyl)-4-[(3S,4R,1E)-4-benzyloxymethoxy-3-hydroxypent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose 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: 98.0%

: 154674-70-1
3-O-(4-Methoxybenzyl)-4-[(R,E)-4-benzyloxymethoxy-3-oxopent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose

: 154674-71-2
3-O-(4-Methoxybenzyl)-4-[(3S,4R,1E)-4-benzyloxymethoxy-3-hydroxypent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose

Guidance literature:: With zinc(II) tetrahydroborate; In diethyl ether; at -40 ℃;
DOI:10.1016/S0040-4039(00)61697-0

Reference yield:

: 96823-34-6
Dimethyl [(3R)-3-benzyloxymethoxy-2-oxobutyl]phosphonate

: 154674-71-2
3-O-(4-Methoxybenzyl)-4-[(3S,4R,1E)-4-benzyloxymethoxy-3-hydroxypent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / LiCl; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 16 h / 20 °C

2: 98 percent / Zn(BH₄)2 / diethyl ether / 6 h / -40 °C

With zinc(II) tetrahydroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In diethyl ether; acetonitrile; 1: Condensation / 2: Reduction;
DOI:10.1039/a905771d

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 154674-71-2
3-O-(4-Methoxybenzyl)-4-[(3S,4R,1E)-4-benzyloxymethoxy-3-hydroxypent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose

Guidance literature:: Multi-step reaction with 4 steps

1: 44 percent / i-Pr₂NEt

2: 90 percent / n-BuLi

3: 96 percent / LiCl, DBU / acetonitrile / 15 h / Ambient temperature

4: 98 percent / Zn(BH₄)2 / diethyl ether / -40 °C

With n-butyllithium; zinc(II) tetrahydroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium chloride; In diethyl ether; acetonitrile;
DOI:10.1016/S0040-4039(00)61697-0