(2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-hydroxy-2-(2-iodo-benzyloxy)-cyclohexanone

Base Information

• Chemical Name: (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-hydroxy-2-(2-iodo-benzyloxy)-cyclohexanone
• CAS No.: 194800-89-0
• Molecular Formula: C₂₇H₂₇IO₅
• Molecular Weight: 558.413
• Mol file: 194800-89-0.mol

Synonyms:(2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-hydroxy-2-(2-iodo-benzyloxy)-cyclohexanone

Chemical Property of (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-hydroxy-2-(2-iodo-benzyloxy)-cyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-hydroxy-2-(2-iodo-benzyloxy)-cyclohexanone

There total 3 articles about (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-hydroxy-2-(2-iodo-benzyloxy)-cyclohexanone 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:

2-iodobenzyliodide (4622-38-2) → (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-hydroxy-2-(2-iodo-benzyloxy)-cyclohexanone (194800-89-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / NaH / dimethylformamide / Ambient temperature

2: Hg(OCOCF₃)2 / acetone; H₂O / Ambient temperature

With mercury(II) trifluoroacetate; sodium hydride; In water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(97)01325-7

Reference yield:

methyl 6-deoxy-6-iodo-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside (87326-88-3) → (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-hydroxy-2-(2-iodo-benzyloxy)-cyclohexanone (194800-89-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / NaH / dimethylformamide / Ambient temperature

2: Hg(OCOCF₃)2 / acetone; H₂O / Ambient temperature

With mercury(II) trifluoroacetate; sodium hydride; In water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(97)01325-7

Reference yield:

(2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-(2-iodo-benzyloxy)-2-methoxy-6-methylene-tetrahydro-pyran (194800-88-9) → (2S,3R,4S,5R)-3,4-Bis-benzyloxy-5-hydroxy-2-(2-iodo-benzyloxy)-cyclohexanone + (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-hydroxy-2-(2-iodo-benzyloxy)-cyclohexanone (194800-89-0)

Guidance literature:

With mercury(II) trifluoroacetate; In water; acetone; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0040-4039(97)01325-7

upstream raw materials:

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

2-iodobenzyliodide

methyl 6-deoxy-6-iodo-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside

Downstream raw materials:

(4R,5S,6R)-5,6-Bis-benzyloxy-4-(2-iodo-benzyloxy)-cyclohex-2-enone

(1R,2R,3S,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-iodo-benzyloxy)-cyclohexanol

Methanesulfonic acid (1R,2S,3R,4S,5S)-3,4-bis-benzyloxy-5-hydroxy-2-(2-iodo-benzyloxy)-cyclohexyl ester

Methanesulfonic acid (1R,2S,3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-iodo-benzyloxy)-cyclohexyl ester