(R)-3-Benzyloxy-3-((2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-propionaldehyde

Base Information

Chemical Name:(R)-3-Benzyloxy-3-((2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-propionaldehyde
CAS No.:370885-74-8
Molecular Formula:C₄₀H₅₆O₆Si
Molecular Weight:660.967
Hs Code.:

Synonyms:(R)-3-Benzyloxy-3-((2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-propionaldehyde

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Chemical Property of (R)-3-Benzyloxy-3-((2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-propionaldehyde

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Technology Process of (R)-3-Benzyloxy-3-((2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-propionaldehyde

There total 11 articles about (R)-3-Benzyloxy-3-((2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-propionaldehyde 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:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 370885-74-8
(R)-3-Benzyloxy-3-((2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-propionaldehyde

Guidance literature:: Multi-step reaction with 9 steps

1: 2,6-lutidine / CH₂Cl₂ / Ambient temperature

2: CSA / methanol; CH₂Cl₂ / Ambient temperature

3: NaH / dimethylformamide / Ambient temperature

4: OsO₄, NMO / acetone; H₂O / Ambient temperature

5: NaIO₄ / tetrahydrofuran; H₂O / Ambient temperature

6: MgBr₂*OEt₂ / CH₂Cl₂ / -78 - 0 °C

7: NaH / dimethylformamide / Ambient temperature

8: OsO₄, NMO / acetone; H₂O / Ambient temperature

9: NaIO₄ / tetrahydrofuran; H₂O / Ambient temperature

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; camphor-10-sulfonic acid; sodium hydride; magnesium bromide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4039(98)02606-9

Reference yield:

: 438002-84-7
(R)-4-Benzyloxy-4-((2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-butane-1,2-diol

: 370885-74-8
(R)-3-Benzyloxy-3-((2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-propionaldehyde

Guidance literature:: With sodium periodate; In tetrahydrofuran; water; Ambient temperature;
DOI:10.1016/S0040-4039(98)02606-9

Reference yield:

: 438002-76-7
(2R,3S,5R,6S)-2-Hydroxymethyl-6-methyl-5-triisopropylsilanyloxy-6-vinyl-tetrahydro-pyran-3-ol

: 370885-74-8
(R)-3-Benzyloxy-3-((2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-propionaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide / 0.25 h / 20 °C

1.2: 35.53 g / dimethylformamide / 16 h / 20 °C

2.1: 5.53 g / aq. OsO₄; N-methylmorpholine N-oxide / acetone / 19 h / 20 °C

3.1: NaIO₄ / tetrahydrofuran; H₂O / 9 h / 20 °C

4.1: 5.24 g / MgBr₂*Et₂O / CH₂Cl₂ / 2 h / -78 - 20 °C

5.1: NaH / dimethylformamide / 0.5 h / 20 °C

5.2: 100 percent / dimethylformamide / 4.5 h / 0 °C

6.1: osmiumm tetraxide; N-methylmorpholine N-oxide / acetone; H₂O / 9 h / 20 °C

7.1: NaIO₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

With sodium periodate; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; magnesium bromide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo010974p