(2S,3S)-2,3-Dihydroxy-3-[(2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-hydroxymethyl-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-2-yl]-propionic acid methyl ester

Base Information

• Chemical Name: (2S,3S)-2,3-Dihydroxy-3-[(2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-hydroxymethyl-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-2-yl]-propionic acid methyl ester
• CAS No.: 197007-78-6
• Molecular Formula: C₅₂H₆₀O₁₅
• Molecular Weight: 925.039
• Mol file: 197007-78-6.mol

Synonyms:

Chemical Property of (2S,3S)-2,3-Dihydroxy-3-[(2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-hydroxymethyl-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-2-yl]-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2,3-Dihydroxy-3-[(2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-hydroxymethyl-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-2-yl]-propionic acid methyl ester

There total 5 articles about (2S,3S)-2,3-Dihydroxy-3-[(2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-hydroxymethyl-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-2-yl]-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:

1'-O-methoxymethyl-2,3,4,3',4'-penta-O-benzyl-sucrose (175289-53-9) → (2S,3S)-2,3-Dihydroxy-3-[(2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-hydroxymethyl-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-2-yl]-propionic acid methyl ester (197007-78-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 66 percent / diisopropylethylamine, DMAP / CH₂Cl₂ / 72 h / Ambient temperature

2: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, room temp., 1 h

3: benzene / 16 h / Ambient temperature

4: 82 percent / Bu₄NF*3H₂O / tetrahydrofuran / 3 h / Ambient temperature

5: OsO₄, NMO / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 48 h

With dmap; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; benzene;

DOI:10.1080/07328309708005741

Reference yield:

{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(2S,3S,4R,5R)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy]-tetrahydro-pyran-2-yl}-methanol (197007-59-3) → (2S,3S)-2,3-Dihydroxy-3-[(2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-hydroxymethyl-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-2-yl]-propionic acid methyl ester (197007-78-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, room temp., 1 h

2: benzene / 16 h / Ambient temperature

3: 82 percent / Bu₄NF*3H₂O / tetrahydrofuran / 3 h / Ambient temperature

4: OsO₄, NMO / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 48 h

With osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; water; tert-butyl alcohol; benzene;

DOI:10.1080/07328309708005741

Reference yield:

(E)-3-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(2S,3S,4R,5R)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid methyl ester (197007-66-2) → (2S,3S)-2,3-Dihydroxy-3-[(2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-hydroxymethyl-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-2-yl]-propionic acid methyl ester (197007-78-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / Bu₄NF*3H₂O / tetrahydrofuran / 3 h / Ambient temperature

2: OsO₄, NMO / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 48 h

With osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; In tetrahydrofuran; water; tert-butyl alcohol;

DOI:10.1080/07328309708005741

upstream raw materials:

(E)-3-[(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-hydroxymethyl-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-2-yl]-acrylic acid methyl ester

1'-O-methoxymethyl-2,3,4,3',4'-penta-O-benzyl-sucrose

{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(2S,3S,4R,5R)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy]-tetrahydro-pyran-2-yl}-methanol

(E)-3-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(2S,3S,4R,5R)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid methyl ester