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

Base Information

• Chemical Name: 3-O-(4-Methoxybenzyl)-4-[(R,E)-4-benzyloxymethoxy-3-oxopent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose
• CAS No.: 154674-70-1
• Molecular Formula: C₂₈H₃₄O₈
• Molecular Weight: 498.573
• Mol file: 154674-70-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 3-O-(4-Methoxybenzyl)-4-[(R,E)-4-benzyloxymethoxy-3-oxopent-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: 96.0%

Dimethyl [(3R)-3-benzyloxymethoxy-2-oxobutyl]phosphonate (96823-34-6) + 3-O-(4-Methoxybenzyl)-1,2-O-isopropylidene-4-formylerythrofuranose (154799-94-7) → 3-O-(4-Methoxybenzyl)-4-[(R,E)-4-benzyloxymethoxy-3-oxopent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose (154674-70-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In acetonitrile; for 15h; Ambient temperature;

DOI:10.1016/S0040-4039(00)61697-0

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → 3-O-(4-Methoxybenzyl)-4-[(R,E)-4-benzyloxymethoxy-3-oxopent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose (154674-70-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 44 percent / i-Pr₂NEt

2: 90 percent / n-BuLi

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

With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile;

DOI:10.1016/S0040-4039(00)61697-0

Reference yield:

2-Methylpropyl (R)-2-(benzyloxymethoxy)propanoate (154674-77-8) → 3-O-(4-Methoxybenzyl)-4-[(R,E)-4-benzyloxymethoxy-3-oxopent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose (154674-70-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / n-BuLi

2: 96 percent / LiCl, DBU / acetonitrile / 15 h / Ambient temperature

With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In acetonitrile;

DOI:10.1016/S0040-4039(00)61697-0

upstream raw materials:

Dimethyl [(3R)-3-benzyloxymethoxy-2-oxobutyl]phosphonate

3-O-(4-Methoxybenzyl)-1,2-O-isopropylidene-4-formylerythrofuranose

(R)-1-[(3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol

3-O-(4-Methoxybenzyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Downstream raw materials:

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

1,2,3-Tri-O-acetyl-4-[(S)-Benzyloxycarbonylamino(methoxycarbonyl)methyl]-D-erythrofuranose

(S)-Benzyloxycarbonylamino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid

methyl 1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-5-[[(phenylmethoxy)carbonyl]amino]-β-D-allohexofuranuronate 2,3-diacetate