[(2R,3R)-3-((2S,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-methanol

Base Information

• Chemical Name: [(2R,3R)-3-((2S,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-methanol
• CAS No.: 87256-51-7
• Molecular Formula: C₃₈H₄₂O₇
• Molecular Weight: 610.747
• Mol file: 87256-51-7.mol

Synonyms:[(2R,3R)-3-((2S,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-methanol

Chemical Property of [(2R,3R)-3-((2S,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3R)-3-((2S,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-methanol

There total 4 articles about [(2R,3R)-3-((2S,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-methanol 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: 90.0%

4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-yl)-but-2-en-1-ol (87256-50-6) → (S)-1-((2R,3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-yl)-ethane-1,2-diol (87256-54-0) + [(2R,3R)-3-((2S,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-methanol (87256-51-7)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; In dichloromethane; at -30 ℃; for 6h;

DOI:10.1016/S0040-4039(00)81894-8

Reference yield:

α-allyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose (81972-19-2,82659-52-7,82659-55-0,82659-57-2,82659-59-4,82659-61-8,92470-94-5) → [(2R,3R)-3-((2S,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-methanol (87256-51-7)

Guidance literature:

Multi-step reaction with 4 steps

1: O₃, NaOAc / methanol; CH₂Cl₂ / -78 °C

2: t-BuOK / tetrahydrofuran / -78 deg C, than 0 deg C

3: DIBAL / CH₂Cl₂ / 0 °C

4: 90 percent / t-BuO₂H, Ti(i-PrO)4, L-(+)-diethyl tartrate / CH₂Cl₂ / 6 h / -30 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; potassium tert-butylate; sodium acetate; diisobutylaluminium hydride; ozone; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)81894-8

Reference yield:

((2R,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetaldehyde (96689-97-3,120520-77-6,120520-78-7,120520-79-8,120520-80-1) → [(2R,3R)-3-((2S,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-methanol (87256-51-7)

Guidance literature:

Multi-step reaction with 3 steps

1: t-BuOK / tetrahydrofuran / -78 deg C, than 0 deg C

2: DIBAL / CH₂Cl₂ / 0 °C

3: 90 percent / t-BuO₂H, Ti(i-PrO)4, L-(+)-diethyl tartrate / CH₂Cl₂ / 6 h / -30 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)81894-8

upstream raw materials:

4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-yl)-but-2-en-1-ol

α-allyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose

((2R,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetaldehyde

Downstream raw materials:

(S)-5-[(1S,2R,3R)-1,2-Dihydroxy-3-methyl-4-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl]-dihydro-furan-2-one

(Z)-(6R,7R)-6-Hydroxy-7-methyl-8-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-oct-4-enoic acid

(S)-1-{(4S,5R)-2,2-Dimethyl-5-[(R)-1-methyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-[1,3]dioxolan-4-yl}-pent-4-en-1-ol

(2R,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-4-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butan-2-ol