methoxy 5-deoxy-3-O-(p-methoxybenzyl)-α,β-erythro-pentofuranoside

Base Information

• Chemical Name: methoxy 5-deoxy-3-O-(p-methoxybenzyl)-α,β-erythro-pentofuranoside
• CAS No.: 109519-13-3
• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.294
• Mol file: 109519-13-3.mol

Synonyms:

Chemical Property of methoxy 5-deoxy-3-O-(p-methoxybenzyl)-α,β-erythro-pentofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methoxy 5-deoxy-3-O-(p-methoxybenzyl)-α,β-erythro-pentofuranoside

There total 3 articles about methoxy 5-deoxy-3-O-(p-methoxybenzyl)-α,β-erythro-pentofuranoside 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: 94.0%

methyl 5-deoxy-3-O-(p-methoxybenzyl)-α/β-D-ribofuranoside (115693-80-6,115793-53-8) → methoxy 5-deoxy-3-O-(p-methoxybenzyl)-α,β-erythro-pentofuranoside (109519-13-3,109519-14-4,132246-24-3,132246-28-7)

Guidance literature:

With acetic anhydride; In dimethyl sulfoxide; for 48h; Ambient temperature;

DOI:10.1039/P19870002681

Reference yield:

(3aR,6S,6aR)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-5-methylene-tetrahydro-furo[2,3-d][1,3]dioxole (132246-21-0) → (4R,5S)-2-Methoxy-4-(4-methoxy-benzyloxy)-5-methyl-dihydro-furan-3-one (109519-13-3,109519-14-4,132246-24-3,132246-28-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / H₂ / Rhodium on alumina / 4 h

2: 1.) MeOH, HCl; 2.) DMSO, Ac₂O

With hydrogenchloride; methanol; hydrogen; acetic anhydride; dimethyl sulfoxide; Rh/Al₂O₃;

DOI:10.1039/P19900003201

Reference yield:

1,2-O-isopropylidene-5-O-methylsulphonyl-3-O-(p-methoxybenzyl)-α-D-ribofuranose (115693-79-3) → (4R,5S)-2-Methoxy-4-(4-methoxy-benzyloxy)-5-methyl-dihydro-furan-3-one (109519-13-3,109519-14-4,132246-24-3,132246-28-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) KI, MeCOEt; 2.) KOBu^t, THF

2: 98 percent / H₂ / Rhodium on alumina / 4 h

3: 1.) MeOH, HCl; 2.) DMSO, Ac₂O

With tetrahydrofuran; hydrogenchloride; methanol; potassium tert-butylate; hydrogen; acetic anhydride; dimethyl sulfoxide; butanone; potassium iodide; Rh/Al₂O₃;

DOI:10.1039/P19900003201

upstream raw materials:

(3aR,6S,6aR)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-5-methylene-tetrahydro-furo[2,3-d][1,3]dioxole

1,2-O-isopropylidene-5-O-methylsulphonyl-3-O-(p-methoxybenzyl)-α-D-ribofuranose

methyl 5-deoxy-3-O-(p-methoxybenzyl)-α/β-D-ribofuranoside

Downstream raw materials:

(4R,5S)-3-Hexadec-(Z)-ylidene-4-(4-methoxy-benzyloxy)-5-methyl-dihydro-furan-2-one

(4R,5S)-3-Hexadec-(E)-ylidene-4-(4-methoxy-benzyloxy)-5-methyl-dihydro-furan-2-one

(4S,5S)-3-Hexadec-(Z)-ylidene-4-(4-methoxy-benzyloxy)-5-methyl-dihydro-furan-2-one

(4S,5S)-3-Hexadec-(E)-ylidene-4-(4-methoxy-benzyloxy)-5-methyl-dihydro-furan-2-one

Refernces

• 1、 Wood, William W.,Watson, Graham M.. "The Total Synthesis of (-)-Litsenolides C-1 and C-2". . p. 2681 - 2688. Retrieved 2007/10/02.