(3R,4S,5R)-methyl 3,4-dihydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate

Base Information

• Chemical Name: (3R,4S,5R)-methyl 3,4-dihydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate
• CAS No.: 1376576-35-0
• Molecular Formula: C₁₀H₁₆O₆
• Molecular Weight: 232.233
• Mol file: 1376576-35-0.mol

Synonyms:(3R,4S,5R)-methyl 3,4-dihydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate

Chemical Property of (3R,4S,5R)-methyl 3,4-dihydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5R)-methyl 3,4-dihydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate

There total 7 articles about (3R,4S,5R)-methyl 3,4-dihydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate 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: 96.0%

(1R,5R,6S)-methyl 5-(methoxymethoxy)-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylate (1376575-69-7) → (3R,4S,5R)-methyl 3,4-dihydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate (1376576-35-0)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; water; at 25 ℃; for 2h;

DOI:10.1039/c2ob25635e

Reference yield:

(R)-methyl 4-((2S,3R)-3-ethynyloxiran-2-yl)-4-(methoxymethoxy)-2-methylenebutanoate (1376576-21-4) → (3R,4S,5R)-methyl 3,4-dihydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate (1376576-35-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / oct-1-ene; ethyl acetate / 6 h / 25 °C

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 14 h / Reflux

3: sulfuric acid / tetrahydrofuran; water / 2 h / 25 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sulfuric acid; In tetrahydrofuran; dichloromethane; oct-1-ene; water; ethyl acetate;

DOI:10.1039/c2ob25635e

Reference yield:

(4R)-methyl 4-(methoxymethoxy)-2-methylene-4-((2S,3R)-3-vinyloxiran-2-yl)butanoate (1376576-24-7) → (3R,4S,5R)-methyl 3,4-dihydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate (1376576-35-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 14 h / Reflux

2: sulfuric acid / tetrahydrofuran; water / 2 h / 25 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sulfuric acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1039/c2ob25635e

upstream raw materials:

(R)-methyl 4-((2S,3R)-3-ethynyloxiran-2-yl)-4-(methoxymethoxy)-2-methylenebutanoate

(4R)-methyl 4-(methoxymethoxy)-2-methylene-4-((2S,3R)-3-vinyloxiran-2-yl)butanoate

(1R,5R,6S)-methyl 5-(methoxymethoxy)-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylate

ethyl (4R)-4-((2S,3R)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-4-hydroxy-2-methylenebutanoate