8-(methoxycarbonyl)octyl O-(4-O-allyl-3-O-methyl-α-L-rhamnopyranosyl)-(1-2)-4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: 8-(methoxycarbonyl)octyl O-(4-O-allyl-3-O-methyl-α-L-rhamnopyranosyl)-(1-2)-4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside
• CAS No.: 121260-40-0
• Molecular Formula: C₃₄H₅₄O₁₁
• Molecular Weight: 638.796

Synonyms:8-(methoxycarbonyl)octyl O-(4-O-allyl-3-O-methyl-α-L-rhamnopyranosyl)-(1-2)-4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside

Chemical Property of 8-(methoxycarbonyl)octyl O-(4-O-allyl-3-O-methyl-α-L-rhamnopyranosyl)-(1-2)-4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-(methoxycarbonyl)octyl O-(4-O-allyl-3-O-methyl-α-L-rhamnopyranosyl)-(1-2)-4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside

There total 9 articles about 8-(methoxycarbonyl)octyl O-(4-O-allyl-3-O-methyl-α-L-rhamnopyranosyl)-(1-2)-4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside 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:

methyl 4-O-allyl-2,3-O-isopropylidene-α-L-rhamnopyranoside (75336-76-4) → 8-(methoxycarbonyl)octyl O-(4-O-allyl-3-O-methyl-α-L-rhamnopyranosyl)-(1-2)-4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside (121260-40-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) trifluoroacetic acid; 2.) M H₂SO₄; / 1.) dichloromethane, 30 min, 0 deg C; 2.) 4 h, reflux;

2: 72 percent / pyridine / Ambient temperature

3: 91 percent / 32percent hydrogen bromide / CH₂Cl₂; acetic acid / 1.5 h

4: ammonia-saturated methanol / methanol / 48 h / Ambient temperature

5: sodium hydride / methanol; tetrahydrofuran / Ambient temperature

6: chlorotrimethylsilane / CH₂Cl₂ / 2 h / Heating

7: 70 percent / silver triflate, 1,1,3,3-tetramethylurea / CH₂Cl₂

8: 1.0 g / dry sodium methoxide / methanol / 1.) 0 deg C, 2 h; 2.) room temp.;

With chloro-trimethyl-silane; sulfuric acid; ammonia; hydrogen bromide; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; trifluoroacetic acid; tetramethylurea; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetic acid;

DOI:10.1016/0008-6215(88)84078-3

Reference yield:

(3R,4S,5R,6S)-5-Allyloxy-6-methyl-tetrahydro-pyran-2,3,4-triol → 8-(methoxycarbonyl)octyl O-(4-O-allyl-3-O-methyl-α-L-rhamnopyranosyl)-(1-2)-4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside (121260-40-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 72 percent / pyridine / Ambient temperature

2: 91 percent / 32percent hydrogen bromide / CH₂Cl₂; acetic acid / 1.5 h

3: ammonia-saturated methanol / methanol / 48 h / Ambient temperature

4: sodium hydride / methanol; tetrahydrofuran / Ambient temperature

5: chlorotrimethylsilane / CH₂Cl₂ / 2 h / Heating

6: 70 percent / silver triflate, 1,1,3,3-tetramethylurea / CH₂Cl₂

7: 1.0 g / dry sodium methoxide / methanol / 1.) 0 deg C, 2 h; 2.) room temp.;

With chloro-trimethyl-silane; ammonia; hydrogen bromide; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; tetramethylurea; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetic acid;

DOI:10.1016/0008-6215(88)84078-3

Reference yield:

1,2,3-tri-O-acetyl-4-O-allyl-L-rhamnopyranose (121260-33-1) → 8-(methoxycarbonyl)octyl O-(4-O-allyl-3-O-methyl-α-L-rhamnopyranosyl)-(1-2)-4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside (121260-40-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / 32percent hydrogen bromide / CH₂Cl₂; acetic acid / 1.5 h

2: ammonia-saturated methanol / methanol / 48 h / Ambient temperature

3: sodium hydride / methanol; tetrahydrofuran / Ambient temperature

4: chlorotrimethylsilane / CH₂Cl₂ / 2 h / Heating

5: 70 percent / silver triflate, 1,1,3,3-tetramethylurea / CH₂Cl₂

6: 1.0 g / dry sodium methoxide / methanol / 1.) 0 deg C, 2 h; 2.) room temp.;

With chloro-trimethyl-silane; ammonia; hydrogen bromide; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; tetramethylurea; In tetrahydrofuran; methanol; dichloromethane; acetic acid;

DOI:10.1016/0008-6215(88)84078-3

upstream raw materials:

8-(methoxycarbonyl)octyl O-(2-O-acetyl-4-O-allyl-3-O-methyl-α-L-rhamnopyranosyl)-(1-2)-4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside

methyl 4-O-allyl-2,3-O-isopropylidene-α-L-rhamnopyranoside

4-O-allyl-1,2-O-(1-methoxyethylidene)-β-L-rhamnopyranose nev

4-O-allyl-2-O-acetyl-3-O-methyl-α-L-rhamnopyranosyl chloride

Downstream raw materials:

8-(methoxycarbonyl)octyl O-(4-O-allyl-2,3-di-O-methyl-α-L-rhamnopyranosyl)-(1-2)-4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside

8-(methoxycarbonyl)octyl O-(2,3-di-O-methyl-α-L-rhamnopyranosyl)-(1-2)-4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside

8-(methoxycarbonyl)octyl O-(3,6-di-O-methyl-β-D-glucopyranosyl)-(1-4)-O-(2,3-di-O-methyl-α-L-rhamnopyranosyl)-(1-2)-4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside

8-(methoxycarbonyl)octyl O-(2,4-di-O-3,6-di-O-methyl-β-D-glucopyranosyl)-O-(1-4)-O-(2,3-di-O-methyl-α-L-rhamnopyranosyl)-(1-2)-3-O-methyl-α-L-rhamnopyranoside

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