Acetic acid (2R,3S,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-ylmethyl ester

Base Information

Chemical Name:Acetic acid (2R,3S,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-ylmethyl ester
CAS No.:512782-04-6
Molecular Formula:C₂₄H₃₉IO₆Si
Molecular Weight:578.56
Hs Code.:

Acetic acid (2R,3S,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-ylmethyl ester

Synonyms:Acetic acid (2R,3S,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-ylmethyl ester

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Chemical Property of Acetic acid (2R,3S,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Acetic acid (2R,3S,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-ylmethyl ester

There total 11 articles about Acetic acid (2R,3S,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-ylmethyl 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: 94.0%

: 512781-99-6
Acetic acid (2R,3S,4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-6-hydroxymethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-ylmethyl ester

: 512782-04-6
Acetic acid (2R,3S,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In toluene; acetonitrile; Heating;
DOI:10.3987/com-01-s(m)6

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 512782-04-6
Acetic acid (2R,3S,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 87 percent / TfOH / diethyl ether / 0.33 h / 20 °C

2: 64 percent / toluene / 0.33 h / -50 - -20 °C

3: 98 percent / 9-BBN; H₂O₂; OH^(1-) / tetrahydrofuran / 12 h / 20 °C

4: 95 percent / tetrahydrofuran; aq. HCl / 1 h / 20 °C

5: 99 percent / imidazole; DMAP / CH₂Cl₂ / 0.5 h / 0 - 20 °C

6: 95 percent / aq. HF / acetonitrile / -20 °C

7: 94 percent / Ph₃P; I₂; imidazole / toluene; acetonitrile / Heating

With 1H-imidazole; dmap; 9-borabicyclo[3.3.1]nonane dimer; trifluorormethanesulfonic acid; hydrogen fluoride; hydroxide; dihydrogen peroxide; iodine; triphenylphosphine; In tetrahydrofuran; hydrogenchloride; diethyl ether; dichloromethane; toluene; acetonitrile; 2: Tebbe olefination;
DOI:10.3987/com-01-s(m)6

Reference yield:

: 143289-36-5
2,3:4,6-Di-O-isopropylidene-D-mannopyranonolactone

: 512782-04-6
Acetic acid (2R,3S,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 79 percent / NaH / tetrahydrofuran / -78 - -40 °C

2: 99 percent / SmI₂; HOCH₂CH₂OH; HMPA / tetrahydrofuran / 0.5 h / 20 °C

3: 87 percent / TfOH / diethyl ether / 0.33 h / 20 °C

4: 64 percent / toluene / 0.33 h / -50 - -20 °C

5: 98 percent / 9-BBN; H₂O₂; OH^(1-) / tetrahydrofuran / 12 h / 20 °C

6: 95 percent / tetrahydrofuran; aq. HCl / 1 h / 20 °C

7: 99 percent / imidazole; DMAP / CH₂Cl₂ / 0.5 h / 0 - 20 °C

8: 95 percent / aq. HF / acetonitrile / -20 °C

9: 94 percent / Ph₃P; I₂; imidazole / toluene; acetonitrile / Heating

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; 9-borabicyclo[3.3.1]nonane dimer; samarium diiodide; trifluorormethanesulfonic acid; hydrogen fluoride; hydroxide; dihydrogen peroxide; iodine; sodium hydride; ethylene glycol; triphenylphosphine; In tetrahydrofuran; hydrogenchloride; diethyl ether; dichloromethane; toluene; acetonitrile; 4: Tebbe olefination;
DOI:10.3987/com-01-s(m)6