3-[(2S,3R,4R,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid methyl ester

Base Information

Chemical Name:3-[(2S,3R,4R,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid methyl ester
CAS No.:685133-02-2
Molecular Formula:C₃₂H₄₃NO₉SSi
Molecular Weight:645.846
Hs Code.:

3-[(2S,3R,4R,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid methyl ester

Synonyms:3-[(2S,3R,4R,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid methyl ester

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Chemical Property of 3-[(2S,3R,4R,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid methyl ester

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Technology Process of 3-[(2S,3R,4R,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid methyl ester

There total 8 articles about 3-[(2S,3R,4R,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid methyl 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:

: 85-44-9
phthalic anhydride

: 685133-02-2
3-[(2S,3R,4R,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: aq. NaHCO₃ / acetone; dioxane / 6 h / 20 °C

2: pyridine / 12 h / 20 °C

3: BF₃*Et₂O / CH₂Cl₂ / 12 h / 20 °C

4: 100 percent / MeONa / methanol / 4 h / 20 °C

5: TsOH / dimethylformamide / 6 h / 50 °C / 15 Torr

6: pyridine / CH₂Cl₂ / 4 h / 0 - 20 °C

7: NaBH₃CN; TMS / acetonitrile / 12 h / 0 - 20 °C

With pyridine; tetramethylsilane; boron trifluoride diethyl etherate; sodium methylate; sodium cyanoborohydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1002/anie.200352919

Reference yield:

: 685132-99-4
3-[(2R,4aR,6S,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylsulfanyl]-propionic acid methyl ester

: 685133-02-2
3-[(2S,3R,4R,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid methyl ester

Guidance literature:: With tetramethylsilane; sodium cyanoborohydride; In acetonitrile; at 0 - 20 ℃; for 12h;
DOI:10.1002/anie.200352919

Reference yield:

: 10022-13-6,31505-44-9,81704-02-1,116347-84-3,131234-07-6,144300-04-9,79733-86-1
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

: 685133-02-2
3-[(2S,3R,4R,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: BF₃*Et₂O / CH₂Cl₂ / 12 h / 20 °C

2: 100 percent / MeONa / methanol / 4 h / 20 °C

3: TsOH / dimethylformamide / 6 h / 50 °C / 15 Torr

4: pyridine / CH₂Cl₂ / 4 h / 0 - 20 °C

5: NaBH₃CN; TMS / acetonitrile / 12 h / 0 - 20 °C

With pyridine; tetramethylsilane; boron trifluoride diethyl etherate; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/anie.200352919