3-C-benzyloxymethyl-3,5,6-trideoxy-1,2-O-isopropylidene-5-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose

Base Information

• Chemical Name: 3-C-benzyloxymethyl-3,5,6-trideoxy-1,2-O-isopropylidene-5-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose
• CAS No.: 98039-21-5
• Molecular Formula: C₂₆H₃₂O₆
• Molecular Weight: 440.536
• Mol file: 98039-21-5.mol

Synonyms:3-C-benzyloxymethyl-3,5,6-trideoxy-1,2-O-isopropylidene-5-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose

Chemical Property of 3-C-benzyloxymethyl-3,5,6-trideoxy-1,2-O-isopropylidene-5-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-C-benzyloxymethyl-3,5,6-trideoxy-1,2-O-isopropylidene-5-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose

There total 13 articles about 3-C-benzyloxymethyl-3,5,6-trideoxy-1,2-O-isopropylidene-5-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose 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: 83.0%

Methyltriphenylphosphonium bromide (1779-49-3) + 3-C-benzyloxymethyl-3-deoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-α-D-ribo-hexofuranos-5-ulose (98039-29-3) → 3-C-benzyloxymethyl-3,5,6-trideoxy-1,2-O-isopropylidene-5-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose (98039-21-5)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

3-C-benzyloxymethyl-3-deoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-α-D-ribo-hexofuranos-5-ulose; In tetrahydrofuran; hexane; for 6h;

DOI:10.1248/cpb.48.1761

Reference yield: 77.0%

3-C-benzyloxymethyl-3-deoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-α-D-ribo-hexofuranos-5-ulose (98039-29-3) + Methylenetriphenylphosphorane (19493-09-5) → 3-C-benzyloxymethyl-3,5,6-trideoxy-1,2-O-isopropylidene-5-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose (98039-21-5)

Guidance literature:

In tetrahydrofuran; for 8h; Ambient temperature;

DOI:10.1039/P19850000019

Reference yield:

3-C-(benzyloxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose (85315-68-0) → 3-C-benzyloxymethyl-3,5,6-trideoxy-1,2-O-isopropylidene-5-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose (98039-21-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 86 percent / p-TsOH*H₂O / dimethylformamide / 4 h / 55 °C

2.1: 95 percent / n-Bu₃SnH; MgBr₂ / CH₂Cl₂ / 1 h / 20 °C

3.1: 87 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 2.5 h / -78 °C

4.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

4.2: 83 percent / hexane; tetrahydrofuran / 6 h

With n-butyllithium; oxalyl dichloride; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; magnesium bromide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation / 4.2: Wittig methylenation;

DOI:10.1248/cpb.48.1761

upstream raw materials:

3-C-benzyloxymethyl-3-deoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-α-D-ribo-hexofuranos-5-ulose

Methylenetriphenylphosphorane

Methyltriphenylphosphonium bromide

p-Anisaldehyde dimethyl acetal

Downstream raw materials:

(2S,3R,4R)-2,4-bis(2,2-dimethylpropanoyloxymethyl)-3,5-[(S)-4-methoxybenzylidenedioxy]pentanal

(2S,3S,4R)-2,4-bis(2,2-dimethylpropanoyloxymethyl)-3,5-[(S)-4-methoxybenzylidenedioxy]pentan-1-ol

(2S,3S,4R)-2,4-bis(2,2-dimethylpropanoyloxymethyl)-5-(4-methoxybenzoyloxy)pentane-1,3-diol

2,2-Dimethyl-propionic acid (4S,5R)-4-[(S)-1-benzyloxymethyl-2-(2,2-dimethyl-propionyloxy)-ethyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-5-ylmethyl ester