5,6-O-(1-Methylethylidene)-3-O-(phenylmethyl)-L-ascorbic acid

Base Information

• Chemical Name: 5,6-O-(1-Methylethylidene)-3-O-(phenylmethyl)-L-ascorbic acid
• CAS No.: 86404-07-1
• Molecular Formula: C₁₆H₁₈O₆
• Molecular Weight: 306.315
• DSSTox Substance ID: DTXSID501183284
• Nikkaji Number: J593.201G
• Mol file: 86404-07-1.mol

Synonyms:SCHEMBL886854;VKOBEVNCBJUIJY-WCQYABFASA-N;DTXSID501183284;86404-07-1;5,6-O-(1-Methylethylidene)-3-O-(phenylmethyl)-L-ascorbic acid;(R)-4-(benzyloxy)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxyfuran-2(5H)-one

Chemical Property of 5,6-O-(1-Methylethylidene)-3-O-(phenylmethyl)-L-ascorbic acid

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 306.11033829
• Heavy Atom Count: 22
• Complexity: 463

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OCC(O1)C2C(=C(C(=O)O2)O)OCC3=CC=CC=C3)C
• Isomeric SMILES: CC1(OC[C@H](O1)[C@@H]2C(=C(C(=O)O2)O)OCC3=CC=CC=C3)C

Technology Process of 5,6-O-(1-Methylethylidene)-3-O-(phenylmethyl)-L-ascorbic acid

There total 15 articles about 5,6-O-(1-Methylethylidene)-3-O-(phenylmethyl)-L-ascorbic acid 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: 86.0%

benzyl bromide (100-39-0) + 5,6-O-isopropylidene-L-ascorbic acid (15042-01-0) → O3-benzyl-O5,O6-(1-methylethylidene)-L-ascorbic acid (86404-07-1)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; dimethyl sulfoxide; at 20 ℃;

DOI:10.1021/jo049319i

Reference yield: 66.0%

benzyl chloride (100-44-7) + sodium L-ascorbate (146-75-8,6381-77-7,6866-66-6,7317-67-1,7378-23-6,21547-69-3,58657-35-5,134-03-2) → 2-C-benzyl-α-L-xylo-hex-3-ulofuranosono-1,4-lactone (1259489-71-8) + O3-benzyl-O5,O6-(1-methylethylidene)-L-ascorbic acid (86404-07-1)

Guidance literature:

benzyl chloride; sodium L-ascorbate; With sodium hydroxide; In water; acetone;

With toluene-4-sulfonic acid; In acetone; for 0.666667h;

DOI:10.1007/s11172-010-0101-8

Reference yield: 60.0%

(R)-3,4-bis(benzyloxy)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)furan-2(5H)-one (2871-84-3) → O3-benzyl-O5,O6-(1-methylethylidene)-L-ascorbic acid (86404-07-1)

Guidance literature:

With ethylaluminum dichloride; In toluene; for 2h; Ambient temperature;

DOI:10.1016/0957-4166(96)00427-2

upstream raw materials:

5,6-O-isopropylidene-D-isoascorbic acid

benzyl bromide

isoascorbic acid

5,6-O-isopropylidene-L-ascorbic acid

Downstream raw materials:

5,6-O-isopropylidene-2-O-acetonyl-3-O-benzylascorbic acid

5,6-O-Isopropylidene-2-O-allyl-3-O-benzyl-L-ascorbic acid

[(R)-4-Benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-oxo-2,5-dihydro-furan-3-yloxy]-acetic acid 2,5,7,8-tetramethyl-2-(4,8,12-trimethyl-tridecyl)-chroman-6-yl ester

3-O-benzyl-2-O-benzyloxycarbonylmethyl-5,6-O-isopropylidene-L-ascorbic acid