((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

Base Information

• Chemical Name: ((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester
• CAS No.: 557088-08-1
• Molecular Formula: C₆₃H₆₆O₁₀
• Molecular Weight: 983.211
• Mol file: 557088-08-1.mol

Synonyms:((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

Chemical Property of ((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

There total 3 articles about ((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester 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: 77.0%

(3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene (102208-53-7) + ((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid (557087-95-3) → ((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester (557088-08-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1021/jo030039x

Reference yield:

1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene (81972-19-2) → ((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester (557088-08-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 56 percent / lithim periodate; lithium phosphate; OsO₄ / ethyl acetate / 24 h / 20 °C / pH 7.0

2: 94 percent / 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

3: 77 percent / 4-DMAP; DCC / CH₂Cl₂ / 18 h / 20 °C

With dmap; lithium phosphate; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; 2-methyl-but-2-ene; lithium metaperiodate; dicyclohexyl-carbodiimide; In dichloromethane; water; ethyl acetate; tert-butyl alcohol;

DOI:10.1021/jo030039x

Reference yield:

(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanal (96689-97-3,120520-77-6,120520-79-8,120520-80-1,120520-78-7) → ((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester (557088-08-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

2: 77 percent / 4-DMAP; DCC / CH₂Cl₂ / 18 h / 20 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; dicyclohexyl-carbodiimide; In dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo030039x

upstream raw materials:

(3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene

((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid

1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene

(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanal

Downstream raw materials:

(2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[2-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-allyl]-tetrahydro-pyran