methyl 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate

Base Information

Chemical Name:methyl 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate
CAS No.:131675-58-6
Molecular Formula:C₃₀H₅₃IO₉Si₂
Molecular Weight:740.821
Hs Code.:

Synonyms:methyl 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate

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Chemical Property of methyl 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate

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Technology Process of methyl 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate

There total 17 articles about methyl 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate 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: 92.0%

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 130851-56-8
methyl 4-<<3-O-methyl-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate

: 131675-58-6
methyl 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -20 - 0 ℃; for 1h;
DOI:10.1039/c39900001275

Reference yield:

: 73-34-7
L-rhamnose

: 131675-58-6
methyl 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate

Guidance literature:: Multi-step reaction with 10 steps

1: Et₃N, DMAP / CH₂Cl₂ / 12 h / 25 °C

2: 93 percent / SnCl₄ / CH₂Cl₂ / 4 h / 0 °C

3: 100 percent / K₂CO₃ / tetrahydrofuran; methanol / 10 h / 25 °C

4: 1.) n-Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 2.) DMF, 25 deg C, 20 h

5: 100 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / 25 °C

6: 70 percent / NBS, H₂O / acetone / 1 h / 25 °C

7: NaH / CH₂Cl₂ / 1 h / 25 °C

8: 95 percent / 4A molecular sieves, BF₃*OEt₂ / CH₂Cl₂ / 1 h / -65 - -50 °C

9: 93 percent / K₂CO₃ / tetrahydrofuran; methanol / 2.5 h / 25 °C

10: 90 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -20 - 0 °C

With 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; 4 A molecular sieve; boron trifluoride diethyl etherate; water; tin(IV) chloride; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; triethylamine; cesium fluoride; In tetrahydrofuran; methanol; dichloromethane; acetone;

Reference yield:

: 131675-54-2
phenyl 3-O-methyl-1-thio-α-L-rhamnopyranoside

: 131675-58-6
methyl 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / 25 °C

2: 70 percent / NBS, H₂O / acetone / 1 h / 25 °C

3: NaH / CH₂Cl₂ / 1 h / 25 °C

4: 95 percent / 4A molecular sieves, BF₃*OEt₂ / CH₂Cl₂ / 1 h / -65 - -50 °C

5: 93 percent / K₂CO₃ / tetrahydrofuran; methanol / 2.5 h / 25 °C

6: 90 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -20 - 0 °C

With 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; 4 A molecular sieve; boron trifluoride diethyl etherate; water; sodium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone;