(R)-1-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol

Base Information

• Chemical Name: (R)-1-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol
• CAS No.: 438002-46-1
• Molecular Formula: C₃₄H₅₂O₅Si
• Molecular Weight: 568.869
• Mol file: 438002-46-1.mol

Synonyms:(R)-1-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol

Chemical Property of (R)-1-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol

There total 8 articles about (R)-1-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol 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:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (R)-1-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol (438002-46-1)

Guidance literature:

Multi-step reaction with 6 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

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:

allyltributylstanane (24850-33-7) + (2R,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-carbaldehyde (438002-45-0) → (R)-1-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol (438002-46-1)

Guidance literature:

With magnesium bromide; In dichloromethane; at -78 - 0 ℃;

DOI:10.1016/S0040-4039(98)02606-9

Reference yield:

(2R,3S,5R,6S)-2-Hydroxymethyl-6-methyl-5-triisopropylsilanyloxy-6-vinyl-tetrahydro-pyran-3-ol (438002-76-7) → (R)-1-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol (438002-46-1)

Guidance literature:

Multi-step reaction with 4 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

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

upstream raw materials:

allyltributylstanane

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

triisopropylsilyl chloride

benzyl bromide

Downstream raw materials:

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

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

[(2R,3S)-3-((2R,3S,4aR,6S,7R,9R,9aS)-6-Allyl-3,9-bis-benzyloxy-2-benzyloxymethyl-9a-methyl-octahydro-1,5-dioxa-benzocyclohepten-7-yloxy)-tetrahydro-pyran-2-yl]-methanol

(2R,3S,4aR,6S,7R,9R,9aS)-6-Allyl-7-((2R,3S)-2-allyl-tetrahydro-pyran-3-yloxy)-3,9-bis-benzyloxy-2-benzyloxymethyl-9a-methyl-octahydro-1,5-dioxa-benzocycloheptene