(3S)-Methyl-4,6-O-benzyliden-2,3-didesoxy-3-C-formyl-α-D-erythro-hexopyranosid

Base Information

• Chemical Name: (3S)-Methyl-4,6-O-benzyliden-2,3-didesoxy-3-C-formyl-α-D-erythro-hexopyranosid
• CAS No.: 100100-71-8
• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.305
• Mol file: 100100-71-8.mol

Synonyms:(3S)-Methyl-4,6-O-benzyliden-2,3-didesoxy-3-C-formyl-α-D-erythro-hexopyranosid

Chemical Property of (3S)-Methyl-4,6-O-benzyliden-2,3-didesoxy-3-C-formyl-α-D-erythro-hexopyranosid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-Methyl-4,6-O-benzyliden-2,3-didesoxy-3-C-formyl-α-D-erythro-hexopyranosid

There total 3 articles about (3S)-Methyl-4,6-O-benzyliden-2,3-didesoxy-3-C-formyl-α-D-erythro-hexopyranosid 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:

Methyl-4,6-O-benzyliden-2,3-didesoxy-3-iod-3-C-<(methoxy)(methoxycarbonylamino)methyl>-α-D-arabino-hexopyranosid (100101-35-7) → (3S)-Methyl-4,6-O-benzyliden-2,3-didesoxy-3-C-formyl-α-D-erythro-hexopyranosid (100100-71-8)

Guidance literature:

With potassium hydroxide; hydrogen; triethylamine; palladium on activated charcoal; Yield given. Multistep reaction; 1.) CH₃OH, 1 at, 3 h, RT 2.) CH₃OH, H₂O, 3 h, reflux;

DOI:10.1002/jlac.198619860403

Reference yield:

methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitromethyl-α-D-ribo-hexopyranoside (38183-78-7) → (3S)-Methyl-4,6-O-benzyliden-2,3-didesoxy-3-C-formyl-α-D-erythro-hexopyranosid (100100-71-8)

Guidance literature:

With titanium(III) chloride; sodium hydride; Yield given. Multistep reaction; 1.) DMF, mineral oil, 0 deg C; 2.) pH 1, 3 min, 0 deg C;

DOI:10.1016/S0008-6215(00)85897-8

Reference yield:

(E)-Methyl-4,6-O-benzyliden-2,3-didesoxy-3-C-methoxymethylen-α-D-erythro-hexopyranosid (100020-19-7) → (3R)-Methyl-4,6-O-benzyliden-2,3-didesoxy-3-C-formyl-α-D-erythro-hexopyranosid (100100-72-9) + (3S)-Methyl-4,6-O-benzyliden-2,3-didesoxy-3-C-formyl-α-D-erythro-hexopyranosid (100100-71-8)

Guidance literature:

With sodium tetrahydroborate; mercury dichloride; Yield given. Multistep reaction. Yields of byproduct given; 1.) acetonitrile, H₂O, room temperature, 90 min, 2.) 0 deg C, 10 min;

DOI:10.1002/jlac.198619860403

upstream raw materials:

methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitromethyl-α-D-ribo-hexopyranoside

(E)-Methyl-4,6-O-benzyliden-2,3-didesoxy-3-C-methoxymethylen-α-D-erythro-hexopyranosid

Methyl-4,6-O-benzyliden-2,3-didesoxy-3-iod-3-C-<(methoxy)(methoxycarbonylamino)methyl>-α-D-arabino-hexopyranosid

Downstream raw materials:

(3R)-Methyl-4,6-O-benzyliden-2,3-didesoxy-3-C-formyl-α-D-erythro-hexopyranosid

methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-<4-(1,3-dioxan-2-yl)-1-butenyl>-α-D-arabino-hexopyranoside

(4aR,6S,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-8-carbaldehyde

Refernces

• 1、 Nieuwenhuis, Jacobus J.,Jordaan, Johannes H.. "THE SYNTHESIS OF C-FORMYL, BRANCHED-CHAIN CARBOHYDRATE DERIVATIVES BY THE CONVERSION OF NITROMETHYL GROUPS INTO CARBONYL GROUPS". . p. 185 - 192. Retrieved 2007/10/02.