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

Base Information

Chemical Name:benzyl 6,3'-O-(2-methyl-5-methylene-benzoyl)-(2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside
CAS No.:522632-93-5
Molecular Formula:C₅₆H₅₆O₁₂
Molecular Weight:921.053
Hs Code.:

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

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

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

There total 9 articles about benzyl 6,3'-O-(2-methyl-5-methylene-benzoyl)-(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: 71.0%

: 522632-92-4
2-Methyl-5-((2R,3R,4S,5R,6S)-4,5,6-tris-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethoxymethyl)-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

: 522632-93-5
benzyl 6,3'-O-(2-methyl-5-methylene-benzoyl)-(2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; for 0.5h;
DOI:10.1002/1099-0690(200301)2003:1<128::AID-EJOC128>3.0.CO;2-S

Reference yield:

: 118-90-1
ortho-methylbenzoic acid

: 522632-93-5
benzyl 6,3'-O-(2-methyl-5-methylene-benzoyl)-(2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 9 steps

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

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

3: 65 percent / NaH / dimethylformamide / 20 h / 20 °C

4: DDQ / CH₂Cl₂; H₂O / 5 h / 20 °C

5: 386 mg / DCC; DMAP / 20 h

6: 85 percent / trifluoroacetic acid / CH₂Cl₂ / 5 h / 20 °C

7: 50 percent / DMAP; DCC / CH₂Cl₂ / 20 h / 20 °C

8: 65 percent / hydrazinium acetate; pyridine / CH₂Cl₂; methanol / 2 h / 20 °C

9: 71 percent / N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / 0.5 h

With pyridine; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; phosphoric acid; boron trifluoride diethyl etherate; hydrogen bromide; hydrazinium monoacetate; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; cyclohexane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1002/1099-0690(200301)2003:1<128::AID-EJOC128>3.0.CO;2-S

Reference yield:

: 72985-19-4
5-(bromomethyl)-2-methylbenzoic acid

: 522632-93-5
benzyl 6,3'-O-(2-methyl-5-methylene-benzoyl)-(2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

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

2: 65 percent / NaH / dimethylformamide / 20 h / 20 °C

3: DDQ / CH₂Cl₂; H₂O / 5 h / 20 °C

4: 386 mg / DCC; DMAP / 20 h

5: 85 percent / trifluoroacetic acid / CH₂Cl₂ / 5 h / 20 °C

6: 50 percent / DMAP; DCC / CH₂Cl₂ / 20 h / 20 °C

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

8: 71 percent / N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / 0.5 h

With pyridine; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; hydrazinium monoacetate; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide;
DOI:10.1002/1099-0690(200301)2003:1<128::AID-EJOC128>3.0.CO;2-S