6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-xylo-hexofuranos-5-ulose

Base Information

• Chemical Name: 6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-xylo-hexofuranos-5-ulose
• CAS No.: 475291-30-6
• Molecular Formula: C₁₈H₂₄O₇
• Molecular Weight: 352.384
• Mol file: 475291-30-6.mol

Synonyms:6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-xylo-hexofuranos-5-ulose

Chemical Property of 6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-xylo-hexofuranos-5-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-xylo-hexofuranos-5-ulose

There total 4 articles about 6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-xylo-hexofuranos-5-ulose 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: 100.0%

6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-gluco-hexofuranose (397870-67-6) → 6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-xylo-hexofuranos-5-ulose (475291-30-6)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃; for 1.25h;

DOI:10.1246/bcsj.75.1927

Reference yield:

1,2-O-isopropylidene-3-O-methoxymethyl-α-D-glucofuranose (104487-62-9) → 6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-xylo-hexofuranos-5-ulose (475291-30-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dibutyltin oxide / toluene / 3 h / Heating

1.2: 88 percent / CsF / dimethylformamide / 13 h / 80 °C

2.1: 100 percent / (COCl)2; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 1.25 h / -78 - 0 °C

With oxalyl dichloride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; In dichloromethane; toluene; 2.1: Swern oxidation;

DOI:10.1246/bcsj.75.1927

Reference yield:

benzyl bromide (100-39-0) → 6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-xylo-hexofuranos-5-ulose (475291-30-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: nBu₂SnO / toluene / Heating

1.2: 95 percent / CsF / dimethylformamide / 50 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

With oxalyl dichloride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; In dichloromethane; toluene; 2.1: Swern oxidation;

DOI:10.1021/ol0171620

upstream raw materials:

6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-gluco-hexofuranose

1,2-O-isopropylidene-3-O-methoxymethyl-α-D-glucofuranose

benzyl bromide

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

((4R,5S)-4-{(4R,5S)-5-[(E)-4-Benzenesulfonyl-8-(2-hexyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-carbamic acid tert-butyl ester

(E)-(4S,5R,6R,7R)-8-Benzyloxy-4,5,6-trihydroxy-7-hydroxymethyl-7-(2,2,2-trichloro-acetylamino)-oct-2-enoic acid ethyl ester

N-[(R)-2-Benzyloxy-1-hydroxymethyl-1-((3aR,5R,6S,6aR)-6-methoxymethoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-2,2,2-trichloro-acetamide

N-[(R)-2-Benzyloxy-1-formyl-1-((3aR,5R,6S,6aR)-6-methoxymethoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-2,2,2-trichloro-acetamide