(3R,5R)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-tert-butoxymethyl-3-methyl-dihydro-furan-2-one

Base Information

• Chemical Name: (3R,5R)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-tert-butoxymethyl-3-methyl-dihydro-furan-2-one
• CAS No.: 223664-66-2
• Molecular Formula: C₃₀H₄₀O₆
• Molecular Weight: 496.644
• Mol file: 223664-66-2.mol

Synonyms:(3R,5R)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-tert-butoxymethyl-3-methyl-dihydro-furan-2-one

Chemical Property of (3R,5R)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-tert-butoxymethyl-3-methyl-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-tert-butoxymethyl-3-methyl-dihydro-furan-2-one

There total 5 articles about (3R,5R)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-tert-butoxymethyl-3-methyl-dihydro-furan-2-one 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:

(5-tert-butoxymethyl-3-methyl-4,5-dihydro-furan-2-yloxy)-tert-butyl-dimethyl-silane (223664-48-0) + Acetic acid (3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester (223664-31-1) → (R)-3-((3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-tert-butoxymethyl-3-methyl-dihydro-furan-2-one + (3R,5R)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-tert-butoxymethyl-3-methyl-dihydro-furan-2-one (223664-66-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; at 0 ℃;

DOI:10.1002/(SICI)1521-3773(19990401)38:7<923::AID-ANIE923>3.0.CO;2-7

Reference yield:

(R)-tetrahydro-5-oxo-2-furancarboxylic acid (53558-93-3) → (3R,5R)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-tert-butoxymethyl-3-methyl-dihydro-furan-2-one (223664-66-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: BH₃*Me₂S / tetrahydrofuran / 20 °C

2.1: H₂SO₄; MgSO₄ / CH₂Cl₂

3.1: tetrahydrofuran / -78 °C

3.2: hexamethylphosphoric acid triamide

4.1: LDA / tetrahydrofuran / -78 °C

4.2: hexamethylphosphoric acid triamide

5.1: TMSOTf / CH₂Cl₂; tetrahydrofuran / 0 °C

With trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; sulfuric acid; magnesium sulfate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 1.1: Reduction / 2.1: Etherification / 3.1: Metallation / 3.2: Methylation / 4.1: Metallation / 4.2: Etherification / 5.1: Substitution;

DOI:10.1002/(SICI)1521-3773(19990401)38:7<923::AID-ANIE923>3.0.CO;2-7

Reference yield:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) → (3R,5R)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-tert-butoxymethyl-3-methyl-dihydro-furan-2-one (223664-66-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: H₂SO₄; MgSO₄ / CH₂Cl₂

2.1: tetrahydrofuran / -78 °C

2.2: hexamethylphosphoric acid triamide

3.1: LDA / tetrahydrofuran / -78 °C

3.2: hexamethylphosphoric acid triamide

4.1: TMSOTf / CH₂Cl₂; tetrahydrofuran / 0 °C

With trimethylsilyl trifluoromethanesulfonate; sulfuric acid; magnesium sulfate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 1.1: Etherification / 2.1: Metallation / 2.2: Methylation / 3.1: Metallation / 3.2: Etherification / 4.1: Substitution;

DOI:10.1002/(SICI)1521-3773(19990401)38:7<923::AID-ANIE923>3.0.CO;2-7

upstream raw materials:

(5-tert-butoxymethyl-3-methyl-4,5-dihydro-furan-2-yloxy)-tert-butyl-dimethyl-silane

Acetic acid (3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester

(R)-tetrahydro-5-oxo-2-furancarboxylic acid

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

Downstream raw materials:

5-[(S)-4-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-iodo-meth-(Z)-ylidene]-4-methyl-pyrrolidin-(2Z)-ylidenemethyl]-4-tert-butoxymethyl-4-methyl-3,4-dihydro-pyrrol-2-one

(S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-(3-tert-butoxymethyl-3-methyl-5-oxo-4,5-dihydro-3H-pyrrol-2-yl)-meth-(Z)-ylidene]-2,3-dimethyl-pyrrolidine-2-carbonitrile

(S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-(4-tert-butoxymethyl-4-methyl-5-thioxo-4,5-dihydro-3H-pyrrol-2-yl)-meth-(Z)-ylidene]-2,3-dimethyl-pyrrolidine-2-carbonitrile

(S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-(4-tert-butoxymethyl-4-methyl-5-oxo-4,5-dihydro-3H-pyrrol-2-yl)-meth-(Z)-ylidene]-2,3-dimethyl-pyrrolidine-2-carbonitrile