methyl 6,3'-O-(2-methyl-5-methylenebenzoyl)-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 6,3'-O-(2-methyl-5-methylenebenzoyl)-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside
• CAS No.: 522633-07-4
• Molecular Formula: C₅₀H₅₂O₁₂
• Molecular Weight: 844.956

Synonyms:methyl 6,3'-O-(2-methyl-5-methylenebenzoyl)-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside

Chemical Property of methyl 6,3'-O-(2-methyl-5-methylenebenzoyl)-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of methyl 6,3'-O-(2-methyl-5-methylenebenzoyl)-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside

There total 7 articles about methyl 6,3'-O-(2-methyl-5-methylenebenzoyl)-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside 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: 73.0%

5-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxymethyl)-2-methyl-benzoic acid (2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (522633-06-3) → methyl 6,3'-O-(2-methyl-5-methylenebenzoyl)-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside (522633-07-4)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at 20 ℃; for 0.166667h;

DOI:10.1002/1099-0690(200301)2003:1<128::AID-EJOC128>3.0.CO;2-S

Reference yield:

ortho-methylbenzoic acid (118-90-1) → methyl 6,3'-O-(2-methyl-5-methylenebenzoyl)-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside (522633-07-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 62 percent / HBr; o-phosphoric acid / acetic acid / 3 h / 115 °C

2: BF₃*Et₂O / CH₂Cl₂; cyclohexane / 1 h / 20 °C

3: 70 percent / Bu₂SnO; TBAI / toluene / 11 h / Heating

4: 75 percent / DCC; DMAP / CH₂Cl₂ / 24 h

5: 90 percent / TFA / CH₂Cl₂ / 4 h

6: 75 percent / DCC; DMAP / CH₂Cl₂ / 20 h / 20 °C

7: 65 percent / hydrazinium acetate / CH₂Cl₂; methanol / 2 h / 20 °C

8: 73 percent / N-iodosuccinimide; triflic acid / CH₂Cl₂ / 0.17 h / 20 °C

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; phosphoric acid; boron trifluoride diethyl etherate; hydrogen bromide; hydrazinium monoacetate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; dichloromethane; cyclohexane; acetic acid; toluene;

DOI:10.1002/1099-0690(200301)2003:1<128::AID-EJOC128>3.0.CO;2-S

Reference yield:

5-(bromomethyl)-2-methylbenzoic acid (72985-19-4) → methyl 6,3'-O-(2-methyl-5-methylenebenzoyl)-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside (522633-07-4)

Guidance literature:

Multi-step reaction with 7 steps

1: BF₃*Et₂O / CH₂Cl₂; cyclohexane / 1 h / 20 °C

2: 70 percent / Bu₂SnO; TBAI / toluene / 11 h / Heating

3: 75 percent / DCC; DMAP / CH₂Cl₂ / 24 h

4: 90 percent / TFA / CH₂Cl₂ / 4 h

5: 75 percent / DCC; DMAP / CH₂Cl₂ / 20 h / 20 °C

6: 65 percent / hydrazinium acetate / CH₂Cl₂; methanol / 2 h / 20 °C

7: 73 percent / N-iodosuccinimide; triflic acid / CH₂Cl₂ / 0.17 h / 20 °C

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; hydrazinium monoacetate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; dichloromethane; cyclohexane; toluene;

DOI:10.1002/1099-0690(200301)2003:1<128::AID-EJOC128>3.0.CO;2-S

upstream raw materials:

5-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxymethyl)-2-methyl-benzoic acid (2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

ortho-methylbenzoic acid

5-(bromomethyl)-2-methylbenzoic acid

5-[methyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid-6-yloxymethyl]-2-methylbenzoic acid

Downstream raw materials:

methyl O-(2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1 - 4)-2,3-di-O-benzyl-6-O-(3-methoxycarbonyl-4-methylbenzyl)-α-D-glucopyranoside

methyl O-[2-O-benzyl-3-O-(3-hydroxycarbonyl-4-methylbenzyl)-4,6-O-benzylidene-β-D-glucopyranosyl]-(1 - 4)-[2,3-di-O-benzyl-6-O-(3-methoxycarbonyl-4-methyl)benzyl]-α-D-glucopyranoside

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