((2S,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-propa-1,2-dienyl-tetrahydro-pyran-2-yl)-methanol

Base Information

• Chemical Name: ((2S,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-propa-1,2-dienyl-tetrahydro-pyran-2-yl)-methanol
• CAS No.: 324530-38-3
• Molecular Formula: C₃₀H₃₂O₅
• Molecular Weight: 472.581
• Mol file: 324530-38-3.mol

Synonyms:((2S,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-propa-1,2-dienyl-tetrahydro-pyran-2-yl)-methanol

Chemical Property of ((2S,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-propa-1,2-dienyl-tetrahydro-pyran-2-yl)-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2S,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-propa-1,2-dienyl-tetrahydro-pyran-2-yl)-methanol

There total 2 articles about ((2S,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-propa-1,2-dienyl-tetrahydro-pyran-2-yl)-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: 71.0%

trimethyl(propargyl)silane (13361-64-3) + 2,3,4,6-Tetra-O-benzyl-methyl-α/β-D-galactopyranoside (324530-37-2) → ((2S,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-propa-1,2-dienyl-tetrahydro-pyran-2-yl)-methanol (324530-38-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 12h;

DOI:10.1016/S0040-4039(00)01653-1

Reference yield:

Methyl-D-galactopyranoside (97-30-3,617-04-9,709-50-2,1824-94-8,2152-78-5,3149-68-6,3396-99-4,6819-48-3,18469-06-2,20550-04-3,22277-65-2,29411-57-2,35437-40-2,35437-43-5,36191-11-4,36191-12-5,39598-79-3,39598-80-6,39598-89-5,51023-63-3,51223-62-2,51224-38-5,51224-39-6,51224-40-9,51224-41-0,51819-81-9,51819-82-0,51819-83-1,56688-81-4,62279-53-2,64281-79-4,64281-80-7,64912-19-2,66101-73-3,78184-90-4,84368-39-8,84368-40-1,84368-41-2,92142-37-5,93302-26-2,103421-28-9,115794-08-6) → ((2S,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-propa-1,2-dienyl-tetrahydro-pyran-2-yl)-methanol (324530-38-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH; Bu₄NI / 4 h

2: 71 percent / TMSOTf / acetonitrile / 12 h

With trimethylsilyl trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; In acetonitrile;

DOI:10.1016/S0040-4039(00)01653-1

Reference yield:

((2S,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-propa-1,2-dienyl-tetrahydro-pyran-2-yl)-methanol (324530-38-3) → (S)-2-{[(1R,4R,7S,12S,13S,14R,15S)-4-(4-Heptyloxy-phenoxymethyl)-13,14,15-trihydroxy-2,5,9-trioxo-10,16-dioxa-3,6-diaza-bicyclo[10.3.1]hexadecane-7-carbonyl]-amino}-pentanedioic acid

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine / 2 h

2: O₃; Me₂S / 8 h

3: CrO₃; aq. H₂SO₄ / acetone / 0.5 h

4: NaOMe / methanol / 1 h

5: EDC; HOBt; NMM / 2 h

6: Pd(PPh₃)4; morpholine / 1 h

7: 50 percent / EDC; DMAP; DMAP*HCl / 0 °C

8: H₂ / Pd/C / acetic acid; tetrahydrofuran; H₂O

With morpholine; 4-methyl-morpholine; pyridine; chromium(VI) oxide; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dimethylsulfide; sulfuric acid; hydrogen; sodium methylate; 4-(dimethylamino)pyridine hydrochloride; benzotriazol-1-ol; ozone; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; water; acetic acid; acetone; 3: Jones oxidation;

DOI:10.1016/S0040-4039(00)01653-1

upstream raw materials:

trimethyl(propargyl)silane

2,3,4,6-Tetra-O-benzyl-methyl-α/β-D-galactopyranoside

Methyl-D-galactopyranoside

Downstream raw materials:

(2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid

(S)-2-[((1R,4R,7S,12S,13R,14R,15S)-13,14,15-Tris-benzyloxy-4-benzyloxymethyl-2,5,9-trioxo-10,16-dioxa-3,6-diaza-bicyclo[10.3.1]hexadecane-7-carbonyl)-amino]-pentanedioic acid dibenzyl ester

(S)-2-((S)-2-{(R)-3-Benzyloxy-2-[((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-propionylamino}-3-carboxy-propionylamino)-pentanedioic acid dibenzyl ester

(S)-2-{[(1R,4R,7S,12S,13R,14R,15S)-13,14,15-Tris-benzyloxy-4-(4-heptyloxy-phenoxymethyl)-2,5,9-trioxo-10,16-dioxa-3,6-diaza-bicyclo[10.3.1]hexadecane-7-carbonyl]-amino}-pentanedioic acid dibenzyl ester