{(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

Base Information

• Chemical Name: {(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
• CAS No.: 197007-59-3
• Molecular Formula: C₆₅H₇₄O₁₂Si
• Molecular Weight: 1075.38
• Mol file: 197007-59-3.mol

Synonyms:

Chemical Property of {(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(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

There total 1 articles about {(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 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: 15.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 1'-O-methoxymethyl-2,3,4,3',4'-penta-O-benzyl-sucrose (175289-53-9) → {(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) + (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-[(2S,3S,4R,5R)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy]-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 72h; Ambient temperature;

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

Guidance literature:

Multi-step reaction with 3 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: Bu₄NF*3H₂O / tetrahydrofuran / 3 h / Ambient temperature

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 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) → (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 (197007-68-4)

Guidance literature:

Multi-step reaction with 3 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

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; benzene;

DOI:10.1080/07328309708005741

upstream raw materials:

tert-butylchlorodiphenylsilane

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

Downstream 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

(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

(2R,3R)-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

(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