(4R,5R)-kohlensaeure-<(5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>methylester

Base Information

• Chemical Name: (4R,5R)-kohlensaeure-<(5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>methylester
• CAS No.: 78469-80-4
• Molecular Formula: C₁₆H₂₂O₆
• Molecular Weight: 310.347
• Mol file: 78469-80-4.mol

Synonyms:(4R,5R)-kohlensaeure-<(5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>methylester

Chemical Property of (4R,5R)-kohlensaeure-<(5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>methylester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-kohlensaeure-<(5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>methylester

There total 1 articles about (4R,5R)-kohlensaeure-<(5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>methylester 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%

1-O-benzyl-2,3-O-isopropylidene-D-threitol (78469-77-9) + methyl chloroformate (79-22-1) → (4R,5R)-kohlensaeure-<(5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>methylester (78469-80-4)

Guidance literature:

With pyridine; In diethyl ether; 1.) 10 min., -20 deg C, 2.) room temp., overnight;

DOI:10.1002/hlca.19810640311

Reference yield: 84.0%

(4R,5R)-kohlensaeure-<(5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>methylester (78469-80-4) → Carbonic acid (2R,3R)-4-benzyloxy-2,3-dihydroxy-butyl ester methyl ester (78469-81-5)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; water; at 70 - 75 ℃; for 19h;

DOI:10.1002/hlca.19810640311

Reference yield:

(4R,5R)-kohlensaeure-<(5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>methylester (78469-80-4) → ((2R,3S)-3-((benzyloxy)methyl)oxiran-2-yl)methanol (78513-07-2,78513-12-9,78513-15-2,84621-89-6,87172-27-8,95672-91-6,98048-62-5,98048-63-6,78469-85-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / p-toluenesulfonic acid monohydrate / tetrahydrofuran; H₂O / 19 h / 70 - 75 °C

2: 1.) CF₃COOH, 2.) pyridine / 1.) methylene dichloride, 15 h., reflux, 2.) 42 h., 22 deg C, methylene dichloride

3: 97 percent / 1N KOH / tetrahydrofuran; methanol / 2.5 h / Ambient temperature

With pyridine; potassium hydroxide; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; water;

DOI:10.1002/hlca.19810640311

upstream raw materials:

1-O-benzyl-2,3-O-isopropylidene-D-threitol

methyl chloroformate

Downstream raw materials:

Carbonic acid (2R,3R)-4-benzyloxy-2,3-dihydroxy-butyl ester methyl ester

((2R,3S)-3-((benzyloxy)methyl)oxiran-2-yl)methanol

(2R,3R)-kohlensaeure-(4-benzyloxy-3-tosyloxy-1,2-butandiyl)ester