Acetic acid (2R,3S,4S,5R,6R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-pent-4-enyloxy-4,5-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-pent-4-enyloxy-4,5-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 143416-48-2
• Molecular Formula: C₃₉H₅₆O₉Si
• Molecular Weight: 696.954

Synonyms:

Chemical Property of Acetic acid (2R,3S,4S,5R,6R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-pent-4-enyloxy-4,5-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4S,5R,6R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-pent-4-enyloxy-4,5-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

There total 7 articles about Acetic acid (2R,3S,4S,5R,6R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-pent-4-enyloxy-4,5-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl 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:

n-Pent-4-enyl alcohol (821-09-0) → Acetic acid (2R,3S,4S,5R,6R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-pent-4-enyloxy-4,5-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (143416-48-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 74 percent / silver triflate, molecular sieves (4 Angstroem) / CH₂Cl₂ / 0.5 h / -20 °C

2: 96 percent / MeOH / NaOMe

3: 87 percent / imidazole / tetrahydrofuran / 11.5 h / Ambient temperature

4: 84 percent / p-TsOH*H₂O / toluene / 1 h / Ambient temperature

5: 1 h

6: 3.45 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 23 h / Ambient temperature

With 1H-imidazole; methanol; 4 A molecular sieve; silver trifluoromethanesulfonate; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; sodium methylate; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)81568-4

Reference yield:

pent-4-enyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside (125367-09-1,125367-10-4,128503-34-4,143416-41-5) → Acetic acid (2R,3S,4S,5R,6R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-pent-4-enyloxy-4,5-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (143416-48-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / MeOH / NaOMe

2: 87 percent / imidazole / tetrahydrofuran / 11.5 h / Ambient temperature

3: 84 percent / p-TsOH*H₂O / toluene / 1 h / Ambient temperature

4: 1 h

5: 3.45 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 23 h / Ambient temperature

With 1H-imidazole; methanol; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; sodium methylate; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)81568-4

Reference yield:

bromide 2,3,4,6-tetra-O-Bz-α-D-galactopyranosyl bromide (188435-38-3) → Acetic acid (2R,3S,4S,5R,6R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-pent-4-enyloxy-4,5-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (143416-48-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 74 percent / silver triflate, molecular sieves (4 Angstroem) / CH₂Cl₂ / 0.5 h / -20 °C

2: 96 percent / MeOH / NaOMe

3: 87 percent / imidazole / tetrahydrofuran / 11.5 h / Ambient temperature

4: 84 percent / p-TsOH*H₂O / toluene / 1 h / Ambient temperature

5: 1 h

6: 3.45 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 23 h / Ambient temperature

With 1H-imidazole; methanol; 4 A molecular sieve; silver trifluoromethanesulfonate; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; sodium methylate; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)81568-4

upstream raw materials:

3,4-dihydro-2H-pyran

Acetic acid (2R,3R,4R,5R,6R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4,5-dihydroxy-6-pent-4-enyloxy-tetrahydro-pyran-3-yl ester

n-Pent-4-enyl alcohol

(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran-3,4,5-triol

Downstream raw materials:

pent-4-enyl 4,6-di-O-benzyl-β-D-galactopyranoside

Chloro-acetic acid (2R,3S,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-5-hydroxy-6-pent-4-enyloxy-tetrahydro-pyran-4-yl ester

pent-4-enyl 2-O-acetyl-4,6-di-O-benzyl-3-O-chloroacetyl-β-D-galactopyranoside

(2R,3S,4S,5R,6R)-3-Benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-4,5-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran

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