(2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-(2,2-dibromo-vinyl)-2-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran

Base Information

• Chemical Name: (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-(2,2-dibromo-vinyl)-2-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran
• CAS No.: 139215-63-7
• Molecular Formula: C₃₀H₃₂Br₂O₆
• Molecular Weight: 648.388
• Mol file: 139215-63-7.mol

Synonyms:

Chemical Property of (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-(2,2-dibromo-vinyl)-2-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-(2,2-dibromo-vinyl)-2-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran

There total 2 articles about (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-(2,2-dibromo-vinyl)-2-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran 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:

methyl 2,3-bis-O-benzyl-4-O-[(4-methoxyphenyl)methyl]-α-D-glucopyranoside (90633-95-7,94827-31-3,90633-90-2) → (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-(2,2-dibromo-vinyl)-2-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran (139215-63-7)

Guidance literature:

Multi-step reaction with 2 steps

1: DMSO, (COCl)2, NEt₃ / CH₂Cl₂

2: 1.) Ph₃P / 1.) CH₂Cl₂, room temperature, 20 min, 2.) CH₂Cl₂, a) 0 deg C, 5 min, b) room temperature, 25 min

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In dichloromethane;

DOI:10.1021/jo00022a039

Reference yield:

carbon tetrabromide (558-13-4) + (2S,3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde (130523-98-7) → (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-(2,2-dibromo-vinyl)-2-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran (139215-63-7)

Guidance literature:

With triphenylphosphine; Yield given. Multistep reaction; 1.) CH₂Cl₂, room temperature, 20 min, 2.) CH₂Cl₂, a) 0 deg C, 5 min, b) room temperature, 25 min;

DOI:10.1021/jo00022a039

Reference yield:

(2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-(2,2-dibromo-vinyl)-2-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran (139215-63-7) → Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-[2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-tetrahydro-pyran-3-yl ester (139195-54-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi / 1.) THF, -50 deg C to 0 deg C, 1 min, 2.) THF, -50 deg C, 30 min

2: 69 percent / triethylsilane / BF₃*Et₂O / acetonitrile; CH₂Cl₂ / 0 °C

3: 89 percent / potassium azodicarboxylate, acetic acid / dioxane / 24 h / Ambient temperature

4: 89 percent / pyridine / DMAP / Ambient temperature

With pyridine; triethylsilane; n-butyllithium; potassium diazodicarboxylate; acetic acid; dmap; boron trifluoride diethyl etherate; In 1,4-dioxane; dichloromethane; acetonitrile;

DOI:10.1021/jo00022a039

upstream raw materials:

carbon tetrabromide

(2S,3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde

methyl 2,3-bis-O-benzyl-4-O-[(4-methoxyphenyl)methyl]-α-D-glucopyranoside

Downstream raw materials:

(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-[2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-tetrahydro-pyran-3-ol

(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylethynyl)-tetrahydro-pyran-3-ol

Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-[2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-tetrahydro-pyran-3-yl ester

C₅₆H₅₈⁽²⁾H₂O₁₀