(3S,4R,5R)-3,4,5-Tris-benzyloxy-1-((2R,3R,5R,6S)-3,5-dihydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-hexan-1-one

Base Information

• Chemical Name: (3S,4R,5R)-3,4,5-Tris-benzyloxy-1-((2R,3R,5R,6S)-3,5-dihydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-hexan-1-one
• CAS No.: 291282-30-9
• Molecular Formula: C₃₄H₄₂O₈
• Molecular Weight: 578.703
• Mol file: 291282-30-9.mol

Synonyms:(3S,4R,5R)-3,4,5-Tris-benzyloxy-1-((2R,3R,5R,6S)-3,5-dihydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-hexan-1-one

Chemical Property of (3S,4R,5R)-3,4,5-Tris-benzyloxy-1-((2R,3R,5R,6S)-3,5-dihydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-hexan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5R)-3,4,5-Tris-benzyloxy-1-((2R,3R,5R,6S)-3,5-dihydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-hexan-1-one

There total 4 articles about (3S,4R,5R)-3,4,5-Tris-benzyloxy-1-((2R,3R,5R,6S)-3,5-dihydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-hexan-1-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: 79.0%

(2R,3R,5R,6S)-6-Methoxy-2-methyl-3-((3S,4R,5R)-3,4,5-tris-benzyloxy-1,1-bis-ethylsulfanyl-hexyl)-tetrahydro-pyran-3,5-diol (291282-27-4) → (3S,4R,5R)-3,4,5-Tris-benzyloxy-1-((2R,3R,5R,6S)-3,5-dihydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-hexan-1-one (291282-30-9) + (2R,3R,5R,6S)-6-Methoxy-2-methyl-3-((Z)-(3S,4R,5R)-3,4,5-tris-benzyloxy-1-ethylsulfanyl-hex-1-enyl)-tetrahydro-pyran-3,5-diol

Guidance literature:

With mercury dichloride; In water; acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)00752-8

Reference yield:

methyl 2-O-tert-butyldimethylsilyl-3,6-dideoxy-α-D-erythro-hexopyranosid-4-ulose (188254-04-8) → (3S,4R,5R)-3,4,5-Tris-benzyloxy-1-((2R,3R,5R,6S)-3,5-dihydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-hexan-1-one (291282-30-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi; t-Bu-ONa / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 47 percent / tetrahydrofuran / 0.17 h / -78 °C

2.1: 90 percent / TBAF / tetrahydrofuran / 8 h / 20 °C

3.1: 79 percent / HgCl₂ / acetonitrile; H₂O / 0.5 h / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; mercury dichloride; sodium t-butanolate; In tetrahydrofuran; hexane; water; acetonitrile; 1.1: Metallation / 1.2: Alkylation / 2.1: desilylation / 3.1: Oxidation;

DOI:10.1016/S0040-4039(00)00752-8

Reference yield:

C31H40O3S2 (291282-23-0) → (3S,4R,5R)-3,4,5-Tris-benzyloxy-1-((2R,3R,5R,6S)-3,5-dihydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-hexan-1-one (291282-30-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi; t-Bu-ONa / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 47 percent / tetrahydrofuran / 0.17 h / -78 °C

2.1: 90 percent / TBAF / tetrahydrofuran / 8 h / 20 °C

3.1: 79 percent / HgCl₂ / acetonitrile; H₂O / 0.5 h / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; mercury dichloride; sodium t-butanolate; In tetrahydrofuran; hexane; water; acetonitrile; 1.1: Metallation / 1.2: Alkylation / 2.1: desilylation / 3.1: Oxidation;

DOI:10.1016/S0040-4039(00)00752-8

upstream raw materials:

(2R,3R,5R,6S)-6-Methoxy-2-methyl-3-((3S,4R,5R)-3,4,5-tris-benzyloxy-1,1-bis-ethylsulfanyl-hexyl)-tetrahydro-pyran-3,5-diol

methyl 2-O-tert-butyldimethylsilyl-3,6-dideoxy-α-D-erythro-hexopyranosid-4-ulose

C₃₁H₄₀O₃S₂

(2R,3R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-3-((3S,4R,5R)-3,4,5-tris-benzyloxy-1,1-bis-ethylsulfanyl-hexyl)-tetrahydro-pyran-3-ol

Downstream raw materials:

(2R,3S,5R,6S)-6-Methoxy-2-methyl-3-((1S,3S,4R,5R)-3,4,5-tris-benzyloxy-1-hydroxy-hexyl)-tetrahydro-pyran-3,5-diol