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

Base Information

Chemical Name: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
CAS No.:512781-99-6
Molecular Formula:C₂₄H₄₀O₇Si
Molecular Weight:468.663
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 10 articles about 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 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: 95.0%

: 512781-98-5
Acetic acid (2R,3S,4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-ylmethyl ester

: 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

Guidance literature:: With hydrogen fluoride; In acetonitrile; at -20 ℃;
DOI:10.3987/com-01-s(m)6

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; dmap; 9-borabicyclo[3.3.1]nonane dimer; trifluorormethanesulfonic acid; hydrogen fluoride; hydroxide; dihydrogen peroxide; 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

: 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

Guidance literature:: Multi-step reaction with 9 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

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; sodium hydride; ethylene glycol; In tetrahydrofuran; hydrogenchloride; diethyl ether; dichloromethane; toluene; acetonitrile; 4: Tebbe olefination;
DOI:10.3987/com-01-s(m)6